Its either "enough" or "too many" depending on what's going on today.  

They have probably appreciated a lot depending when bought them.

It really depends on what a slight difference is. 

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.

I like the idea of no pets and that is decent income (depending on what the rents are).

Depending on the application, first, last, security, and another month or two.

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

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.

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