My wife and I have a 9.46ac parcel in Umatilla (Lake Co) FL that is a lot smaller but we've explored similar options.  

There are good tax benefits, but you should really decide on whether you want to own and operate a business that requires as much upkeep as STR before exploring it further.

Alternatively, consider a cash-out refinance to access equity without triggering capital gains or explore a 1031 exchange to defer taxes by purchasing another investment property.This post does not create a CPA-Client relationship.

The strategy involves using the HELOC for a flip to generate fast cash, reinvesting profits into long-term rentals, or exploring alternative ventures like short-term rentals or partnerships.

If direct bookings are an important part of your business strategy, it might be worth exploring other platforms or reaching out to VRBO for further clarification on their monitoring practices and commission policies.Hope this helps!

@Andrew MaturanaTo gain a competitive edge in the hospitality industry, explore creative ventures, Triple Net investments, house hacking, syndications, joint ventures, and leverage business acumen, networking, and resources.Good Luck!

Furthermore, you should explore checkbook control versus having the custodian make all the investments.  

I’ve made a conscious effort in automating and digitizing more of my rental management tasks and can share some of the tools I've been exploring that might be helpful to others.I use Baselane a lot, it is a platform that's really geared towards landlords and real estate investors.

This community is a great place to explore financing options and connect with like-minded investors.

You might explore partnerships where you fund all-cash deals in exchange for a portion of the profit.