Given your background, especially with your general contractor's license and hands-on experience with rehabs, transitioning more into real estate seems like a natural progression.Here are a few thoughts:Potential of Real Estate vs.

Naturally your relinquished property will have to sell prior to taking title to the replacement, but this would put you in a better position for a successful exchange.

This is a normal procedure and the business type does not officially matter for this strategy.  

Natural disaster history and insurance options8.

That is just human nature and I get it. 

Here is what I proposed:Setup fees : Administration Setup:One Time Fee: $400Guidebook: Using professional photos give the guests a professional tour of the house and how the home works (Wifi passwords // How to use grill // How to use propane fireplace // Hot tub instructions // Sauna instructions //Check in and check out instructions //where extras may be storedOTA (Online Travel Agency) setups: taking professional photos and actively updating your listing on popular platforms;PMS (Property Management System) Setup Smart Pricing Set upWebsite integrationOther (furniture arrangement / design / décor shopping and set up) $50 per hour· Placement fees · Marketing Cost: Variable depending on needs/wants for marketingFacebook AdsGoogle Ads Cleaners: Set up procedures/take pics of expectations· Management fee—30%Guest communicationCleaner communicationSetting Rental rateDealing with small maintenance issuesBooking CoordinationSmart Lock integrationKeeping supplies stocked (TP, paper towel, all cleaning products, coffee, filters, creamer, sugars, teas,)(Receipts would be submitted on a monthly basis for either reimbursement or book keeping purposes)Encouraging guests to leave good reviews by periodically checking in, providing a review template, and ensuring guests receive the amenities they are looking forContinued marketingMajor Maintenance fees—OwnerCleaning and laundry services fees: Cleaning fee to the guest depending on how cleaner wants to charge

Most of the wholesale offers I’ve received state clearly they want it fully assignable (vs seller approval to assign) and mode of access or specific procedures for access.

More so, each accountant has their own procedures and interpretations.

In some cases title companies will still refuse to insure if they notice something off procedurally with the the tax sale process.

Something like a USDA live-in flip might get you the capital to look at a 5% down multi or something of that nature.