Item: Dropbox Business
Rating: 7
Author: Aaron Pinsker

Use Cases and Deployment Scope

I use Dropbox for a number of my clients, and for most it's on the basic level of simply being able to store files both in the cloud and on the computer locally, as well as to easily share files and folders with other Dropbox users. One of my clients uses Dropbox extensively throughout the organization for a plethora of reasons. Many users in the organization have both a laptop and a desktop, and Dropbox allows them to keep their files in sync b/w the two computers. In addition, Dropbox is integrated with a Windows Server machine with what I call a "master" Dropbox account. On the server, their are shared folders for each user in the organization - for select users, these user folders are also linked to their Dropbox account. This allows for select users to have access to Dropbox, while still storing files on the server for non-Dropbox users to access.

Pros and Cons

Dropbox is one of the best tools to sync files b/w multiple computers. It's easy to install and integrates nicely with both macOS and Windows based system, as well as Linux systems (though it is a bit more complicated of an install process).
Dropbox has a an intelligent and easy to understand conflicted file system. If one file is opened in two locations at once, Dropbox automatically creates a duplicate of the file entitle "[filename] [computer name] conflict copy [date]" - wherein the [filename] is the name of the file, the [computer] name is the name of the computer that generated the conflicted copy, and the [date] is the date the conflicted copy was made. This an invaluable tool to prevent information from being lost or over written.
Dropbox has a versioning system, wherein pervious versions of a file can be accessed via the web interface. Version history also includes the ability to recover accidentally delete files. Both version history and file recovery stores files for 120 days.
A unique aspect of Dropbox for Business (not found in the consumer version) is "Smart Sync." Smart Sync allows for you entire Dropbox folder to be visible on your computer at all times, but files are downloaded intelligently downloaded to save space on the local drive. If a file is stored in the cloud, but no not he computer, the minute you open the folder on the computer the file will download. Smart Sync also allows you to select files and folder to mark them as always local - meaning they will always be available both in the cloud and locally. Smart Sync is an invaluable tool when a users Dropbox folder contains more data than the local hard drive can handle.
Dropbox has a fairly robust admin console, wherein you can manage users, add users, delete users, and even temporarily login as a user to view their Dropbox data without needing to know their password (or having to reset it).
Dropbox supports two factor authentication, which can be enforced on a per user basis as well as organization wide basis, greatly increasing security.
Dropbox provides integration with Microsoft Office, allowing for more than one person to be accessing an Office file simultaneously, and thus able to collaborate directly with the file.
Team folders is a great feature that allows you to create a specific folder for a department or team within an organization. Dropbox members can be added to a specific team, and immediately have access to the team folder without it needing to be manually shared with said member. In addition, folders within a Team folder can be shared with other members outside of the team.

Dropbox support, while relatively responsive, is not always the most helpful. Often times, support will simply link you to knowledge base files without digging more into the issue. When you can elevate your issue further, it often times tech support multiple days to respond to your inquiry.
Dropbox is not technically supported on Windows Server machines. While it installs and appears to work just fine, if any issue occurs with it, Dropbox support won't help you. I have never be given a real reasons as to why Dropbox is not officially supported.
Dropbox recently raised their prices rather substantially and created a two tiered business option. Originally, Dropbox for Business was $10/user/month (with a minimum of 5 users), and provided access to all the admin features that were available at the time. However, now the two tiers are Dropbox for Business Standard and Dropbox for Business Advanced. Standard is now $12.5/user/month with a minimum of 3 years and Advanced is $20/user/month with a minimum of 3 years. While Standard is not that much more expensive than the previous price, Standard includes substantially less features than what were originally available. If you want all of the advanced features that were previously available, you must purchase the Advanced tier - which is double the price of what it used to be.
Dropbox's auto-update feature is extremely frustrating. You have ZERO control over how or when Dropbox updates. There is no option to manually check for updates, and there is no option to turn auto-updates off. On more than one occasion, an update has caused Dropbox to close and NOT re-open. Often times, users don't realize Dropbox has quit until they notice Dropbox no longer syncing.
When a sync error occurs with Dropbox, finding the underlying issue isn't always easy. Often times the Dropbox notification icon will simply state that a file can't sync do to "Access Denied." The file name is given, but not the path to the file name, nor the underlying reason of the "access denied" error.
One of the biggest frustrations with Dropbox is that you can't create a shared folder within an existing shared folder. For example, you have a folder "shared_a" that you have shared with a number of people within your organization. Inside of "shared_a" is a folder "shared_sub_a" that you would like to share with a number member of your organization. You would like this person to be able to see "shared_sub_a" but not "shared_a." Unfortunately, this is currently not possible to do. You can create a completely separate folder and share that with multiple people - but that is a far more cumbersome way to do things. Team folders help to alleviate this issue somewhat (see the Pros section), but it is far from an ideal experience.

Return on Investment

ROI for Dropbox is a difficult thing to measure. For some small organizations I manage, say 3-4 users, it has been easier to simply user Dropbox than implementing an in-house system. While an in-house system may cost less in the long run, one of the benefits of Dropbox is a certain amount of peace of mind of not having to deal with the technical back end.
For a large organization, cost becomes a major consideration. One organization I manage currently has 15 Dropbox users. The organization is using the Advanced tier for Dropbox of Business (and the tiers are an all or nothing thing - you can not have some users on the Standard Dropbox for Business and others on the Advanced - it's either all Standard or all Advanced) - which comes out to $3600/year, a not unsubstantial amount.
In-house systems (using either a central server with VPN access, or other software such as GoodSync) will typically cost more initially, but for a large organization, lifetime costs will often be less - even factoring in potential downtime and tech support needs.
The main thing you or your organization needs to consider when looking at Dropbox is are the features, benefits, ease of implementation, and overall peace of mind worth the rather large monthly and yearly fees vs. implementing a different system. This is not an easy question to answer. However, if a cloud-based syncing solution must be used, Dropbox is one of the best options out there.

Alternatives Considered

Apple iCloud, OneDrive, Box, Google Drive and GoodSync

Both OneDrive and Box offer similar services and features as Dropbox, but I have found Dropbox to be easier to implement and setup than either. In addition, Dropbox can actually cost less than Box when paying yearly vs. monthly. OneDrive for Business has the added benefit of being overall less expensive, and also having deep integration with Office 365. However, most features are only available on Windows, and there is no Linux version at all. In addition, the OneDrive admin console is unnecessarily dense and complex.

iCloud is really a non-starter for business as it is primarily a consumer product that lacks any central management features at all.

Google Drive can be a good option if your organization is invested in Google's G Suite - but the initial size of a Google Drive is 30GB, and adding more storage gets expensive quickly. In addition, Google Drive is primarily geared toward those using Google Docs, Sheet, etc. and thus is primarily geared toward those accessing it via a web interface. While a desktop client is available, it is clumsy to use.

GoodSync is a great alternative if your organization wants to implement an in-house syncing solution.

Performance

Dropbox generally performs quite well. Syncing b/w computer and cloud is generally quick, even for large files - and Dropbox does a good job at managing bandwidth to not use all available bandwidth. In addition, Dropbox includes a LAN based syncing mechanism, so two computers on the same network can sync files via LAN vs. over the internet. Dropbox's webpages always to seem to load quickly and display files, even in a folder with large amount of files, quickly. Dropbox's web-based search though is often times slow and inaccurate.

Usability

Dropbox is relatively easy to install and manage, and when done properly is very much a set it and forget solution. Because Dropbox can integrate directly with an Operating System - whether it be Windows, macOS, or Linux - accessing Dropbox's more advanced features (such as sharing files and folders with other Dropbox users) can be done directly within Windows Explorer or the Finder, etc. via either a right-click or a dropdown menu. The biggest downside to Dropbox, however, is when something does go wrong, it can be difficult to pinpoint the problem. The desktop interface is fairly barebones (by design), and Dropbox does not keep consistent log files.

Likelihood to Recommend

If all your organization needs is an easy to setup and reliable way to sync files and folder b/w multiple computers, Dropbox sync engine is second to none. In addition, if you primarily work with other users, both within and without your organization, Dropbox makes it extremely easy to share files and folders with other users. There are some well designed and easy to use admin and management tools that make managing your organization fairly easy to do. Compared to other services (such as Microsoft's OneDrive or Box), the admin center is well laid out and easy to understand.

When used within a small organization - maybe a dozen employees - implementing Dropbox and scaling it out to your users is a fairly easy thing to do. However, in larger organizations, especially in an organization that is already using a centralized server for file sharing, implementing Dropbox is a far more time consuming tasks - and can take a certain amount of trial and error to implement it in the most effective way possible.

In addition, cost is a major consideration. At $12.5/user/month or $20/user/month (both if billed yearly - $15/month or $25/month if done a month-to-month basis), costs can add up quickly.

Dropbox for Business - powerful and efficient, but expensive and support leaves a lot to be desired.

Overall Satisfaction with Dropbox Business