Lastly, you are also correct that selling the home right back to the homeowner is likely going to get you into trouble.There is no such thing as a "backwards short sale" that is just some guru's play on words to make someting sound fancy that is not even legal.That said, you can certainly find an upscale home where the homeowner needs to short sale it, negotiate the short sale and then sell to another party for a $50k profit.

From the research I've done, it seems there is a frenzy in the "big" markets like LA, NYC, etc that has pushed cap rates on fancy Class A buildings to ridiculously low levels, while the "secondary" and "tertiary" markets have far better deals out there if you really want to make cashflow.This seems odd to me.

Fancy!

Currently I use excel with some VB code to get fancy but have been thinking about making an access database to store everything.

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Unless the building and area are high end the finishes and appliances do not need to be expensive or fancy,  and in fact expensive appliances and finishes are often harder and more expensive to maintain. 

Don't need anything super fancy, just something easy to install/use.I'm a bit overwhelmed with options so any guidance or suggestions you all have would be great!

It sounds fancy but it is just a piece of paper that documents the "current arrangement" for each unit -- the monthly rent, monthly due date, utilities, lease expiration, etc.

Dress well, but comfortable.

No need to be fancy.