We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Can you recommend any specific groups or meetups that you've found valuable?

Would you recommend one over the other?

I'd recommend speaking with a fellow househacker like @Matt Solis.

All three are oceanview properties eligible for STR usages but in areas that we don’t normally fully recommend prospecting as there are either partial usage limitations or waitlists to nightly rental permit and permission.

@Juliette Olsen professional property management is my recommendation.

I hope to learn quickly and over time provide value to them in return through future deals.I'm of course open to recommendations, referrals, criticisms, and advice. 

The Midwest and Southeast would be your best bet but under $100,000 is pretty challenging to find these days unless you go to really bad parts of town, which I would recommend avoiding unless you're a specialist. 

This is not a recommendation or advice, just letting you know about this.

House hacking a 4 plex is what I often recommend to people getting started.