COVID has definitely tightened things up.  

@Gabe Christiansen I’ll shine some light on this thread for you, as I am a licensed mortgage lender. 3% down payment for conventional loans only apply to single family, full review condos, not limited review, or town homes, for first time homebuyers. 5% down payment for conventional loans, up to a 4-plex is attainable through Freddie Macs Conventional loan program called Home Possible, if and only if you fall within the income restrictions.

Flying in town is my top priority, once Covid restrictions ease up.

There can be many other restrictions.

I'm looking to avoid HOAs/deed restricted and want to be careful of town restrictions on short term AirBnBs.

There a bunch of addditional restrictions/burdens to properly using a LLC. 

Because of pent up demand the listings at booked or have been taken off market due to travel restrictions.

We are in uncertain economic times, lending could tighten up making it harder to get a cash out refi.

I looked into the units available over the last few days and it seems a bit too risky for a first purchase as it really restricts any possible exit strategies if the seasonal rental didn't work out.

For example, sales of homes worth $1 million and over are up 88.1% in the past year, as wealthy urban dwellers purchase properties elsewhere to escape pandemic-related restrictions and social unrest.