The Support angle
My personal view on MS SQL is that I do not relish supporting any version of it. I'd argue that for most installations, it is overkill for what is needed. I regularly get called upon to run updates for a well-known accounting system which uses MS SQL as its database engine simply because there is usually an incomprehensible error or two that prevents normal operation thereafter. One recent update involved migrating to a newer version of MS SQL which was complicated by lack of space on the C drive of the server.
The acid test for me when writing or recommending software is: how quickly can we get back up and running should some catastrophe occur? This risk assessment needs to take into account versions of program, ditto data, licencing issues, operating system it can run on, access to installation images, etc., etc. If forced to get a new pc off the shelf from a nearby retail outlet to get the business up and running again, how quickly will we be in a position to process data again, including satellite pc's, without having to resort to software vendor support for installation procedures peculiar to their system as these situations often unfold outside normal office hours? In the above case the support hotline is second to none when speaking to them, but it can take several hours to get to that stage.
One point to bear in mind to ask is if it is possible to schedule such updates so that they are done at a time to suit everyone? If the cloud is where the data is stored, is there this option, or are you forced to update when it suits the vendor's agenda, rather than yours? Accountancy firms in particularly have bad times to be thinking about doing updates, such as the forthcoming Self Assessment deadline.