When I'm evaluating a tool or process to recommend to others I'm guided by the following assumptions, principles and requirements. Of course each organization is unique so the relative importance of each will vary and other selection criteria may be critical - that's why discussing your specific needs is beneficial.
Every organization appropriately wants to spend its money on its primary mission, not on those functions that support it. It's usually difficult, as well, to attract donors for the 'uninteresting, but necessary' office and technology operations.
For most small organizations staff are spread very thin, with responsibilities in many areas and never enough hours to do everything. Again, serving the mission of the organization rightfully has the highest priority. Time spent on support activities must either directly improve the ability to address the mission, or must free time from routine tasks so that the mission can be addressed.
How does any proposed change support the mission, directly or indirectly? If there isn't a clear positive answer then there's no point in the change.
Making available important:
Services
Something that could not be accomplished before with the resources available.
e.g. direct contact with the organization's audience, or online fundraising, or remote collaboration.
Information
e.g. information about your donors such as their location, their interests. OR, the effectiveness of campaigns or services.
Freeing staff time for mission-critical work:
Reduce time required for routine work
e.g. scheduling, mailings, bookkeeping, response to inquiries.
External Costs
First Cost
How much you pay up front for a piece of software, equipment, or an online service.
Operating Cost
How much you pay on an annual basis to maintain, upgrade, re-license, or repair the technology.
Internal Costs
Value of staff time
The actual cost of time spent on the activity at the salary rate including benefits
Opportunity costs
The value of those (usually non-technology) things that could have been accomplished with the time devoted to the technology activity.
Life Cycle cost combines these two
Life cycle costing when done fully includes the "discounted" value of future dollars. It's seldom necessary to go through the analysis effort for technology activities, though for larger capital purchases it can be very worthwhile.
Learning to use new technology should involve minimal training time
My experience says that more than half a day spent on training has to produce a very big benefit to make it worth taking time away from other activities.
The benefits of new technology should be immediately obvious to the users. If they aren't obvious then longer term perseverance is unlikely.
Any new technology should allow easy recovery from mistakes or hardware failure
Backup
Data should be backed up, ideally off-site. It should be easy to restore it as well.
Undo steps
It should be easy to "undo" or "reverse" any mistake during use of the technology. This isn't always possible, but for really big changes you should at least be warned and should be able to return to a previous state, if only by "restoring" a backup.
Data must be exportable
For software one should assume that at some point you'll have to stop using that software, either because the manufacturer stops supporting it, hardware changes, or because you find something better. Making sure that you can export your data in a "neutral" format that can be imported into other software programs is highly desirable.
My experience is that it's most efficient for a staff member to speak with a live person to solve problems or learn new capabilities. The following are my suggested order of usefulness:
On staff - someone in the same office is good, but it's unlikely small offices will have the expertise.
Phone - Phone calls tend to be easy, though describing the problem can be difficult.
Zoom, MSTeams and other platforms greatly enhance a phone call, particularly with screen sharing.
Online Chat - Chat programs are often very helpful because there's a record of what's said and because there isn't the delay experienced with forums and email. Chat is now built into Teams, Zoom, and other tools
Remote logon - Using a remote login service can allow a trusted individual to troubleshoot and fix computers. This article recommends several as of 2021. I have used the free version of TeamViewer.
Forum - Many technical subjects have online "forums" where you can ask questions and receive answers. They often help, but the delay can be frustrating.
Email - My experience with asking questions by email is that it works well occasionally, but is often frustrating because of the delays.
Update: 12/2/2021