The town is encouraging home ownership, so buying a condo/single, living in it for a year plus and then renting out works fine here (what I did), whilst house hacking a multi is more complex.

. - Are most of your loans short-term/interest-only, or are they more complex (e.g., longer-term, amortized, require escrow, commonly modified b/c of prepayments, etc.)? 

Final comment, it seems complex.  

In my experience that either means there is something prohibitive in the zoning, or there simply is not much demand for that sort of product if most people either go with an apartment in a large complex or rent a SFR.

This sounds complex, and if the conclusion you're coming to is mortgage fraud, I would not recommend it. 

For the first time in years I’ve noticed many of the larger apartment complexes even offering the first month free to fill vacant units, so it’s clear that demand is down.

In my experience, a suit for specific enforcement of a real estate purchase contract is not particularly complex or fact intensive that would lead to extensive time needed for discovery. 

On the other hand, I am aware of a few students who thought they would start out small and work their way up, but realized that their first deal could very well be a 60+ unit apartment complex.

Whether you need a CPA with just three rentals depends on the complexity of your situation and your comfort level with DIY tax prep.If things are pretty straightforward, you might be fine with tax software for now.

He flipped houses, built apartment complexes etc....so that's where me wanting to do all of this comes from.