I tell people that real estate investing with me is more like a disease than an occupation.

Key is to make sure you are not cash poor.What I am seeing right now in some sub2 FB groups and a few posts here on BP is people who got close to 100% financing on properties, have a tenant in them but need a major repair and have no funds for that repair. 

You're investing there, paying taxes, making friends, bringing your friends and hoping to create a safe space for others to visit where the people on the other end of the line live full time. 

To be fair, judging by the “ask about the guru” posts on here, many people might not realize this.

Companies and people/investor change overtime so it's not a bad idea to see if they're still the best fit for how you would like to see the properties managed.

There are quite a few people doing Sub-To and owner financing opportunities. 

So often you see a bland 'beach/ocean' themed STRs...I get it, people are booking your condo to go to the beach and relax, but you can have a fun, stand out theme that still revolves around the ocean, relaxation, etc.

However, from discussions with banks on about similar topics, I would say yes it is possible.My understanding is that you both would have to use the property as your primary residence, and you both would have to apply together on the loan application.  

Welcome to BP Steven,These forums are a great place to learn and meet people, whether you're just starting out or you're a seasoned investor.

It's dealing with people; usually upset people, and managing a lot of things at once.