My wife Tawnya and I have been contemplating investing in Real Estate for years, and just last month purchased our first investment property.  

I am contemplating purchasing a long term rental condo in Hilo on the Big Island, having recently sold my house in California.

Though I contemplated it earlier this year, I can’t see the juice being worth the squeeze.

We were contemplating the idea of adding back the kitchen and renting it out on AirBNB since it clearly isn’t eligible for long-term traditional rental as it’s not a legal unit; the ceilings are too low (77 inches high) and there’s only one exit (among a few other things).Would AirBNB be a legitimate option for a unit like this?

HUD views the SAFE Act's requirements for registration and licensing as not applying in this context, which is distinguished from the commercial context contemplated in the SAFE Act.

If the transaction is feasible, the property owner (“Seller/Taxpayer”), selling ownership ofthe property/capital asset to a dedicated trust (the “Trust”) that is set up specifically for the Seller/Taxpayer and the contemplated transaction.

@Daniel Torres  I agree with the   " don't let tax tail wag the dog"  unless you have VERY SIGNIFICANT monies or abilities to buy multi million dollar type properties.  1031 generally works in HIGH appreciating markets or with properties one has owned for decades. you don't see much of it with lower end cash flow homes.. by lower end I mean anything at about 100k or under. the tax benefits at a few hundred grand in my mind are not even worth contemplating.

I'll be curious to hear how it goes for you as a part time RE agent, as I've been contemplating a similar strategy.

I'm contemplating cashing out my self-directed IRA and being done with the non-recourse loan business. 

This is really a personal comfort level decision that requires contemplating many variables and options.