First just want to state, she is your girlfriend not your wife, which is very different in regards to financial status/situation.For me its simple, I am buying this asset and taking on the risk of renovating it and as part of it will be seeking to earn income from it to better myself in the future as I know a W2 job and a 401k does not get you far in retirement.

I am not sure what the status of it currently is — already capped, I imagine.So based on my current circumstances, and in alignment with your suggestion, I was thinking that the best option would be for me to continue to live in this condo, continue saving up, and then combine my savings + pull equity from this prop to invest in an affordable investment property when I can, ideally after a year or so.

Hes one of the bigger " players" in Ft Myers, also owns ( I assume still does) Social, top " clubs/ restaurants there.

You need to reach out and get update on status.  

@Ryan Anders Galveston is generally more welcoming to short-term rentals (STRs) due to its status as a tourist destination.

I don't keep printed copies of their social, date of birth, driver's license, etc.

Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Sounds like some of the folks on here are under playing the true status of the SWFL market...

I have a 2 bed 1 bath garden unit, I have this possible tenant who is interested, she makes about $3500 with disability and social services.

Join local real estate meetups, online forums, and social media groups for advice and insights.