It really depends on what a slight difference is. 

I plan to continue to invest in a mix of both RE syndication and our own rental properties going forward depending on what makes the most sense and offers the best returns. 

He's been out a long time and updates the information regularly based on the market and new applications & tools.

You will have enough for a small downpayment on each option, depending on the area chosen in each case, and you won't have much of a cushion after closing costs. 

My dad and I (both with access to VA loans) are about to get into the multifam game and how we proceed is really going to depend on the true occupancy rules for the VA and our lender.

It seems like each option could work depending on your long-term goals for those assets.

Rent probably around 1400-1500/month depending on finishes and exact location.The number simply don't work well in Huntsville right now.

They have a form you can fill out and submit, might be able to do it online depending on the city.  

Depending on your area, it can be a pain to set up multiple LLCs and keep them running.

A general rule of thumb though (not a hard rule) is that if a market has a prolonged history of vacation rentals such as towns whose commerce is very dependent on tourism like beach or mountain towns, then there is a good chance than those towns have established their airBNB regulations decades ago and are likely stable.