You picked a great community to join.. have you checked out local comps to gauge the market vibe yet?

The STR market here has become way more saturated and competitive especially in San Juan. 

Study the market.

There aren't any good wholesalers in the Cleveland market.

Raising money is all about marketing and sales (not real estate specific) so either hire marketing agency and read sales books, or hop on some LinkedIn courses on marketing and sales.Not sure the legal structure to use: talk to accountants and attorneys.Need deal flow: talk to brokers and go to a lot of networking events.Lending terms: start calling banks and loan brokers.From there, it is all risk mitigation. 

It affects the marketability/value of the property. 

Like any investment, due diligence on the market, asset, financing, and sponsor is critical, and working with an advisor to vet these options is worthwhile.I’ve recently helped several investors transition into 721 UpREITs as a gradual tax-deferred exit from direct ownership.

Are they at market rent, or locked into below-market rates?

Any marketing should always be based on the information provided by sellers in a deal. 

I'd recommend speaking with local specialists in your target market to look at multiple investment options side-to-side.Lastly, some of my clients have been encouraged to stay away from HELOCs unless they expect a lump sum (inheritance, sale of other asset, bonus, etc.) to pay off the HELOC in the next year or 2.