Ray,
What you need to think about is what about the person who comes after me. Will they be computer literate? Will they be comfortable using any program other than e-mail? Will they even have a computer (don't laugh, we have some residents who don't own one)? Will they keep the program updated? Will they have the operating system that the program requires?
If it's a stand alone program, will the Association purchase the computer? What about licensing agreements if they don't purchase the computer? What about printers? Will the computer go home with people or stay in an office? etc.
Who is going to manage the website? Who will set it up? Who will update it (not only now but 10 years from now)?
Our Association is composed of 130 lots. We use pen and paper ledgers to track assessment payments. The Treasurer uses excel for reports (which comes with MS Office). Everyone uses MS Word and those who utilize other word processors saves it as an MS word document.
We had one person set up a database with Microsoft Access for our Architectural files. I could tell that they spent a lot of time on it by developing the different menus and entering data. When I saw it, nobody had updated it for 4 years. Appears many didn't have MS Access on their computer and those who did have it were unaware of how to use the program. We used this as an example of what happens when the next person comes into the job. Therefore, we opted to create paper files and organize them with classification folders. Now, anyone (even if they have zero computer experience) can do the job.
Our Association maintains a website which also allows the Association to use Association e-mail accounts. However, everyone tends to use their own e-mail instead.
A high school student initially set the site up for us. I have expanded what is available on the site but worry who will actually maintain it when I stop. I suspect that it will simply stay as is, not updated and, as I remove my credit card from the account - the site will simply no longer exist as nobody will think of renewing it.
Regardless of what you decide to use, keep it simple and easy to operate with little to no computer experience.
Here are some threads where this has been discussed previously:
Subject: Small HOA software package Subject: HOA Database Software Application Subject: HOA Software Subject: HOA software suggestions Subject: Budget Software Subject: HOA Software same title but a different thread
Subject: Software There are others. If click on the Search icon (big magnifying glass)at the top of this page and type in the word software you will get more than enough info.