I’m based in Tampa and run Graystone Investment Group, focusing heavily on helping (out of state) investors find and manage properties here in Florida.Totally agree on the importance of understanding those short-term rental rules in Florida—each area can feel like its own little country with all the different regulations!

I would add that the problem extends beyond Class D properties.Twice I rented B class rentals to Section 8 residents. 

Also a lot of the "deals" in the Subto community are highly overpriced and charging more than market price most of the time.IF you are still curious or would like to see, I am happy to connect with you, show you the Subto videos and trainings if you'd like from the courses.

You’re asking the right questions, and it’s great to see you thinking strategically.My Take on Your SituationSince you already own a rental and want to expand your portfolio, your main decision points are:1.How to pull equity to fund your next deal2.Whether to transfer your current rental into an LLC3.How to position yourself for long-term growthHere’s how I’d approach it:HELOC vs.

Do you think a duplex is generally a better investment than a single-family home for rental purposes?

I have a degree in civil engineering and 15 years construction, site development, and short term rental experience and am looking to shift my focus/career towards real estate development, mainly raw land although if there were a house on the property could include fix and flip.I plan to purchase 50+ acres of raw land with 1000+ feet of road frontage, have it surveyed and split into separate 5+ acre parcels for re-listing.

We currently have two rental properties, both owned in our names not in LLC. 

In Fayetteville you have relatively inexpensive houses in an area with a high rental population due to Fort Bragg.

I upgraded to premium listing on Zillow rentals.

One paid off (worth around 1.4m) student rental.