I too am in the medical field and looking for a way to retire before I am 40.

But when it came time to come ashore the first thing we did was to buy a primary residence with the express thought to live in it while rehabbing and then after a bit move and turn it into a rental or sell and take the sec 121 primary residence exemption.  

Price $5MMDown 20% ($1 MM)Interest ~6% (which I inflated)30 yr fixed 8-year property tax exemption (already approved)3,390 sf of retail space150 underground parking spaces Monthly payment ~$24k It will be a brand new 5-story 163-unit apartment complex (the builder is the seller).

Based on the scenario you describe only the SFR that is owner occupied would be eligible for capital gains exemption.

Because the credit score will be lowered drastically by things that a landlord can (for the most part) ignore - Macy's CC, Sears CC, medical collections for example.But you don't get that type of report with the service you are using ...

The note can't be called due when transferring to a spouse because transfers to spouses are exempted in the law (exemption #6, I think).

Owner occupants selling are exempt from the SAFE Act licensing issues.

Form 982 was used to report the insolvency to the IRS. and exempt that income from any tax.

You may get TI with everything they find as exemptions, then clear up the existing liens and any claims when you sell with a warranty deed.

I obtained my Agents license (broker in colorado) to do fix and flips, but have had some medical/financial setbacks and am not in a position to wait six months or so for the cash flows of fix/flips.