Introduction and question on getting started

[Aaron Nash]

Hello BP Forum!

I'm Aaron Nash from Orlando, FL and have been listening to the podcasts for some time now.  I own a sports car racing team and prep shop but have a growing interest in real estate and other businesses in general.  Through the Bigger Pockets community I was able to meet and work with Cole Ordiway from the Asheville, NC area.  I reached out to the community and ultimately Cole on behalf of my girlfriend who was in the market for a vacation home around the Asheville area.  Cole knocked it out of the park on all accounts and she was able to secure her dream vacation home.  I can't say enough good things about our first experience with Bigger Pockets and Cole as our real estate guide.  That being said, I'm ready to attempt my first purchase of a home with the intention of growing this into a small portfolio of housing scenarios.  I need advice on the best approach for this goal and am reaching out to the BP community again.

Currently I own a home in the Altamonte Springs, FL area which is a primary residence for my daughter and I.  The mortgage is under my deceased wife's name though I control the asset through power of attorney gained via the legal system here.  The home is currently valued around the 350K mark I believe and we owe about 85K at 4.5% interest on the mortgage.  It was outfitted to be handicap accessible before my wife passed and I believe that might be an advantageous point for future renters or owners.  I think that I want to keep this home for ever and treat it as a rental whether long term lease or short term like Airbnb or the likes.  I've setup an Airbnb host account and marketed the place to get a gauge of how it would do and believe we got a very positive test.  I ended up shutting it down temporarily as I couldn't keep up with requests in combination with not being ready or able to vacate to allow guests in.  In this scenario I would like to purchase a primary residence home for us to live in here in the area so that my daughter can remain in the current school system.  Ideally this is on a lake or with some property for a small shop space.  I don't have much cash saved up for a down payment.               

So I think the question is: Do I keep this home and leverage our appreciation or do I sale it and 1031 into my next primary residence?  Side note: I've recently purchased 5 acres of vacant land in the Hawthorne, FL area which is very close to Gainesville, FL.  I'd like to add several "shed homes" or "container homes" and Airbnb this as well.  I'm open to sale this "as is" alternatively.  Any help or opinions are greatly appreciated.  Thank you!

Aaron Nash