And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

High taxes, a declining population, and an environment that is less than friendly to businesses are important factors to consider.

I'm seeking to be in an environment with like minded individuals to learn and network to grow my portfolio and eventually network to collaborate on larger deals once I have a better understanding of the commercial side. 

Situated on a 0.52-acre lot, the property provides a spacious environment.

I recognize there are other ways I could invest this cash (including another property) but I am being mindful of levering myself out too much in the current environment where job losses are more common in my industry (tech).

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

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.

I am most comfortable with long-term rentals, but I would like to try a flip or two to build my capital.

I have not purchased property via their platform but I'd also note it's few and far between to try to find any deals that pencil in the current environment.  4-5 years ago one could find good cash flow with SFR properties.

so those owners are pretty comfortable - no mortgage payment - and they don't need to sell, and they don't care where an investor "needs" the price to be to make money.