Nicholas, as long as you live in one of the units for at least one year, then you should qualify for an FHA loan.

Section 162 prohibits deducting of educational expenses if they qualify you for a new trade or business.

@Ann CoveyYou will still need to qualify for the loan - meaning they will underwrite you to make sure you can afford the payments

Unless I missed something then ypu qualify for the 121 exclusion.

I believe I could qualify for an FHA loan, but I’m not sure if I would qualify if I used a co-signer.

They are pretty cheap ($80/month) and I have had good luck with them funding qualified tenants.

@Michell ChaseThe main difference between W2 and 1099-R income is that you have a much easier path to qualifying as a Real Estate Professional without a W2 job.Whether or not qualifying as REP will be helpful to you is case by case. 

From a tax perspective, 30 day rentals wont qualify as STR.

Also, the buyer's DTI ratio does not qualify for conventional funding.

Most of the deals that I'm underwriting for clients or for myself struggle to qualify for DSCR loans or pencil out because there's a misalignment between what a property can command in rent and what the monthly debt service will be.