Totally not efficient, but its something we may have to do.

I’ve used seller financing as both a buyer and a seller and it can make a lot of sense in certain circumstances (for example I used it as a buyer when I reached the maximum number of conventional loans I could get, and I’ve used it as a seller to both increase my net proceeds (due to collecting interest as “the bank” in addition to the sales proceeds) and to lessen my capital gains tax hit by spreading it out over a few years).

Speed and cost/tax-efficiency are usually mutually exclusive.  

A friend of mine recently uncovered a pocket listing in La Mesa that hadn’t even hit the MLS.

The 4 real estate cylces have been hit.

Essentially, a 1031 exchange is that neat little trick in the U.S. tax code letting you swap out one investment property for another “like-kind” property, all without taking a tax hit upfront.

Either1) your startup takes off and you can distribute profit fast enough to pay off your debts, or2) you find another source of $100,000 a year (which barely even starts to pay down the $300k, but might provide a better chance for a better loan), or3) you BK and possibly lose the rental houses to creditors (hopefully not, but we don’t know how they are held), or 4) you sell the houses, take the tax hit, work with the IRS on a payment plan whose interest will be much lower than your CCs, and focus on the startup.  

But I hit a wall.First: Trying to find out what similar properties in the area (10 m radius) rent for, I used rentcast and rentometer for this, but they gave me two very different results.

I tell every Chicago investor who calls me about Milwaukee to stay in Chicago - the economic delta is just not big enough to take on the remote cost and efficiency burden.

From experience I can say that it is way harder, you have to find absolute home run deals instead of base hit deals and do often take on much higher risk.