Since I am entering this field in the latter part of my life (63), I do not want 'long-term' investments as I am not interested in making millions, but having enough for the remainder of my life to 'Vive La Vida Loca'!

However, its downfall (and what makes it so easy) is that it is a single-entry system.This means there are no checks and balances to ensure all transactions are entered correctly.

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

You can arguably make it work in any market.

I analyze intensely the ARV price points in my target markets for at least 9 months before I buy. 

No one has a "crystal ball" to time the market perfectly. 

Buyers and sellers should consider some amount of closing money be held in escrow after closing to cover potential problems with the non-responding tenants.Does anybody have any experiences to share with successful use of a Tenant Estoppel Letter, or times they wish they'd know about this tool before entering a Purchase and Sale Agreement?

Markets like Texas (San Antonio or Dallas) or North Carolina (Charlotte) could offer better cash flow with lower costs.

Isn't this happening in many markets thought?

I know when Roofstock first entered the Memphis market, their properties flew off the shelf/site like Costco rotisserie chickens.