So, I'm interested in the Kissimmee Florida area for a potential retirement home.

Saving $10 to miss out on proper data that leads you to a $40k deal is not worth it. 

I have a good FT job in education administration, but I want to retire asap, focusing on RE (so, not really retiring, but you get the idea).

Their property sat vacant for a few months while their guy "saved them money".

I've consistently written about the forces of nature and her current and future effects on the real estate market (even while often being ridiculed and politicized on this very site for it) regardless: I personally moved and invested in coastal Oregon in 2018 from Venice Beach Los Angeles partly as a result of the trajectory of climate and have assisted several clients that specifically purchased on the Oregon Coast for their own 'climate havens,' investment and future retirement homes. 

I don't know how much money tenant has in checking / savings / 401K, etc.

I get asked all the time, what can I do with $10k and my answer is "save more"  At least in my world of buy and hold $10k is not going to do much.  

Sometimes those small gestures can save you headaches when construction dust starts flying.I’m curious... now that you’ve pulled off this deal, how would you approach finding your next project differently, and what kind of local contacts would you prioritize connecting with first?

More doors means less vacancies and it might motivate you to save up and buy a new SFR when you are ready to settle down.

California landlords can now enjoy streamlined maintenance and cost savings thanks to AB 2622.Signed into law in September 2024, AB 2622 raises the threshold for unlicensed contracting work from $500 to $1,000.