You might think your situation is common but if timing was during offseason months, it may work out better for you. You might want to consider a dedicated, trusted Realtor to work closely together and you may be able to find what you're looking for now instead of later.
It sounds like you have some awareness of Naples, since your parents live in the Glades. That's a plus. And seems like you have a good sense for what you would like in a home, location, and community. All positive. So would it be worth just doing some work in advance now with a Realtor -- and then look in Dec when you are down here?
Consider also that prices are increasing. And it's forecasted to increase even more rapidly as we get into season months. So it may be beneficial for you to buy sooner than later. And plus then you could avoid challenges of finding an owner willing to rent during prime season months at lower rent amounts and at a property that is a perfect match for your investment desires.
I'd anticipate you'd be able to get a nice home up to 260k in cash. I have listings that match your desires. I'm sure I could find others too. But my owners are looking to sell now and not likely to rent. If it were a Buyers market and listings were not selling rapidly, then they may be open to renting. But sales are incredibly strong, and stronger than in years.
I just had a couple moving from MA who didn't know the market. We worked together to get to know their desires and I set them up on a free service I offer my customers that allowed them to identify homes they like, and to also get a good sense for the market over a short period of time. The result was they were just here for 1 week and bought their home for 850k. Surely that shows it must have worked to instill high confidence. I think they'd be happy to talk to you about their experience. I'm sure they'd have glowing testimonials.
In the meantime, I can see if I can find anything that may work to fit your desires for RTO in a good investment potential.
Please send me an email. I can send you anything I find -- and set you up for that free service I mentioned. I look forward to hearing from you and helping you find your home near your parents in the Glades.
Nancy Jaynes, Realtor "I Find What You're Looking For"
Multi-Award Winning Top Producer
Premiere Plus Realty Co 370 12th Ave S Naples FL 34102