How can I get bookings in this type of environment in the dead of winter? 

This is especially helpful since your goal is to replace your income and invest full-time.Market Timing: Bend, OR, has seen strong appreciation, but if you believe the market is peaking or stabilizing, now might be a strategic time to cash out.Cons:Losing the Low-Interest Loan: Your 3.1% rate is a huge advantage in today’s environment.

What do YOU look for when roaming a new environment for that purpose?

there are multiple cities across the Midsouth that make for solid investments and you are still able to even see some cashflow even in today's environment without buying just straight up high risk properties. 

Affordable housing in not built by driving rents down, that probably will result in a slum like environment.

Personally due to the rate environment, I am sitting at 65% LTV on my properties, but I also stopped buying and started private lending (in the US at least, I just bought a house in Portugal).You're in a really good position here, it'll just take some math, homework with banks, and diligence in renter underwriting to end up with a fantastic income property and portfolio. 

Urban areas can definitely be tough to gauge from a google maps search because environments are street by street, block by block.  

Smart idea staying flexible in this environment.

Given current cap rate expansion, and the interest rate environment, it would require a significant capital infusion to refinance now.  

I agree, shorter-term plays are tough in the current environment, and patience paired with a strong strategy often leads to success, unfortunately this is a strategy that a lot of real estate investors don’t really have the experience and the patience to follow.