Naples FL "slow flipper" with 2 questions for locals

[Mark Baker]

My wife and I have pulled off a slow flip strategy a few times now and our next target is Naples Florida. We've done faster flips and landlording, but this slow flip approach offers us the lifestyle we desire and that's what we're optimizing for.

Generally, we find a nice 1990s-ish home that needs basic updating (paint, carpet, open up the floor plan, kitchen, etc.)... Wemove-in, improve it, get bored, sell it and re-invest somewhere else that offers a lot of lifestyle benefits.

We have high cash flow remote work day jobs and we like spending our time in amazing places (like Naples/Boulder/San Diego/Sedona)... so this is our strategy to deploy our cashflow to buy/improve assets and grow equity while enjoying where we want to be.

Our plan includes us becoming Florida residents and living in/working on the Naples property during the snowbird season... we will probably leave it vacant during the off-season while we had back to our summer spot we're simultaneously flipping.

Personal enjoyment is the top priority which is probably different from most people who seem to focus on short-term rentals and cashflow. Personally, having short-term rentals as neighbors is one of our fears. Our goal is not casfhlow...  It's a buy, improve, hold for 5-10 years for appreciation and enjoy the heck out of warm winter beaches & Naples.

Our budget is in the $600k - $900k range.  And it doesn't have to be a flip... I'm not a contractor and don't particularly enjoy painting or remodeling, lol. 

okay, here are the questions...

1) What quiet/local (non Airbnb) neighborhoods/neighboring communities should we look at? Specifically through the lens of retaining their value in 5+ years.  Those timeless neighborhoods that will always be desirable, even after a long downturn in the market?

Amenities we are looking for include:  .25 acre or larger, pool with Florida room, private feel to the yard (established trees/hedges/etc), quiet, no possibility of airbnbs or vacationer parties next door... We don't golf, no plans for a boat, but I understand these amenities may be important to future buyers. Bicycle-friendly is a plus for us.

One idea I've had is getting into a neighborhood that would connect to the proposed "Paradise Coast Trail"....  In a perfect scenario, I would show up in October, park the car and e-bike everywhere... To the beach, to the organic markets, coffee shops, restaurants, etc...  That's some dream-life stuff right there.

2) Are there any local property management companies that specialize in monthly rentals during the season?  Our plan is to rent a place starting in October through December... Maybe for the entire season.  I'd much rather work with a local business than AirBnB or VRBO...  Any tips there?

Tried to keep this short... lol. Thanks for reading!

All in all, looking to meet and connect with local investors, RE professionals and to get some local insights if possible.

Cheers!