Changing careers can certainly be a challenge, but it sounds like you're equipped with a solid foundation thanks to your sister's support.

I also don't like the sardine effect where your just packed in a building, ocean lakes is tight with homes but still feels private at the house(s), golf cart community and 2 min from the ocean on a golf cart where ours are.

Our team works exclusively with out-of-town investors and have the support program in place to help build a strong portfolio.

They talked a good story, but their investor support was very lacking.

@Alex MinterWelcome to the Bigger Pockets community! 

Even if these relationships don't go anywhere, you'll get a lot from just having a couple of calls.Next I would try to find some local investment groups/communities and try to chat with as many investors as you can to get an idea how other's started out in your market.

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Quote from @Penny Wilkinson: I'm in a community of 10,000 and deal with this quite often.

I'm in the process of comping duplexes vs condos, but was hoping for community input on any local factors I might be missing.  

In the meantime we are talking to the property manager to find other STR's in the area so we can support a fair market STR rent.