I know some friends and family in that area that have had their houses double or triple in value in the past few years.We also own a cottage in the Muskoka, ON region and are throwing around the idea of a tear-down and rebuild in the 2000 square foot range, which would be about a million dollar investment. 

The best we have is ADU's but even that's challenging because most of the SFH in older neighborhoods have small lots and rarely any garages big enough to rebuild.

I'm looking to see if anyone has found an underwriting model to do deal analysis for tear down/rebuilds, fix-flips or ground up development for SFR.

., rebuild the thing.Secondly, a great deal has to do with where the property is.

With my last deal my bank told me I’d maxed out my DTI and so now I have to look for alternative financing once I rebuild my coffers.

$10K for tree removal and rebuild driveway sounds fair. 

If he put in the effort, he could surely find a private landlord with a 3bed they could squeeze into for cheap just to get by while he continues to save, rebuild his credit, and prepare to buy.

Tearing down and rebuilding would be sort of like doubling down on a "bad" investment.

Wait until you need to muck out a place and rebuild after a hurricane.

They offer month-to-month cancelation, instead of minimum 6-12 months, also they provide coverage for actual cash value instead of full rebuild value.