Here's some input to help guide the decision between selling or renting the property, considering the specifics of the property and the potential additions like the ADU (Accessory Dwelling Unit):1.

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. 

Even with 10% down you’re “hoping” that’s all you lose if it all goes wrong. 

As I build my career as an agent, I’m also passionate about real estate investing, specifically with a goal of purchasing multi-family, buy-and-hold properties where I can live in one unit and rent out the others.I’m here to network, learn from experienced investors, and contribute to the community.

Real estate is definitely a constant learning experience, and adaptability is key.Building connections with buyers in a new market can be a real challenge, especially when trying to understand their specific needs and earning their trust.

I like the idea of san juan, specifically miramar, santurce, or anything 1-2km from the beach with food/entertainment really. 

When you specifically mentioned STR experience and the possibility of something with some added "personal value" bells started going off. 

We don’t know any PMCs to recommend in the Cape Coral/fort Meyers area, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

May I ask why you are specifically looking for smaller deals? 

Many older homes were built without closets.From appraisal today:"The Code refers to "habitable rooms" not bedroomsThe essence of the 2015 International Residential Code is that the code does not specifically use the term bedroom, but refers to all habit- able areas of a home.