I'd talk w/them and get a feel for their circumstances if they talk freely but I would not pry. 

My question is- what if life circumstances change and I need to sell the owner occupied portion within that 3 year window?  

If you have a high DTI ratio because of the student loans, you can still qualify with up to 56.99% back end DTI on an FHA loan. 15% down will not be enough for a DCSR or Hard Money loan based on your circumstances.

Ultimately, separate renter's insurance provides better protection, minimizing confusion and ensuring proper coverage for unforeseen circumstances, benefiting both landlords and tenants.

I have a strict cancellation policy and put this language in my house rules:"Please read and understand AirBnB's cancellation and extenuating circumstances policies.

I also don't get involved with Buyers as the contract language and specifics should be reviewed by an attorney Absolutely, I would never recommend a subject to to a client (or at least not unless under very, very unique circumstances and lots of disclosures).

The strategy of wholesaling is appealing to me based on my current circumstances.

But in certain circumstances it might be a good business decision.

Real Estate Investment is the most neglected segment of real estate agency by a looooong shot.

My goal is to get this ship off the ground and save almost all the money I make from wholesaling to invest in cash flowing rental properties, so once I do make these deals and become successful and circumstances were ever to change for whatever reason, My income isn't only fixed on my ability to "Get a deal" to go through.Anyone willing to toss me a bone on this will be valued more than you'd understand.