Good Day to you.... looking at your badge cant tell what level of expirence you have.  I say start with the basic it's free after that many of your questions wil be answered.  Watch the tech help videos after that Richard points you in the direction to the free videos that will help cover the topics.  
Best of luck

Christine it sounds like your needs are pretty simple so you might get by with the Check Register.
If you need to invoice the homeowner and then track payments you might want to also look at the Invoicing video.

Once you have your "one at a time" system set up and working for the individual homeowner it wouldn't be an issue to use For Next Loops  to step through or Loop through your HOA members and create / print / email them all at once.  
BUT... Baby steps.  You need to learn to crawl before you can run.  Start simple and add on.  Don't attempt to build it all at once.
Really though the sky is the limit.  The system you build can be as simple or enriched as you want to make it.