I have a good team helping me, I have a good system, I’m confident in my ability to talk to sellers because I’m a real estate agent and just am nervous that I should be trying to reach more people.

Don't talk yourself into a place because of personal use.Buying a $475k condo that brings in 35k in gross rental income will lose a lot of money.

Don't disqualify yourself without talking to an expert. 

Otherwise, talk to your bank or credit union.

There is another STR owner in this community I've talked to, and he's been doing it for 1-2 years and he said it's still been a real pain to deal with. 

Talk to the seller, but options are to cancel the sale (and risk losing your deposit), renegotiate to lower the price to allow you to fix the problems or ask them to fix it. 

I notice that you mention two different states when you are talking about house hacking.

You really need to talk to a tax advisor in this situation.

we are setting up two OZ funds and would love to talk about what you've found. one is for land development and is more active the other is passive real estate ownership of extended stay. all are ground up. 

When talking to my FL lawyer he stated any beach equipment or toys you have can be used as an avenue to sue if they get hurt with it, even if previous guess left them so he added a paragraph on beach toys/equipment.