BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

A few of them also mentioned that they don't really expect this to affect the housing affordability in the county, but do believe that STRs can affect the quality and integrity of the neighborhoods in the county which they want to preserve.  

If you don't care about income and are more of a capital gain kind of guy, prices are already high (as you noticed) and there's plenty of land available to buy so I'm not sure how much is left in the tank.

The risk is too high of losing everything.

Here’s some context: Property 1: >$100k in EquityValue: $325kDebt: $220k @ 2.88% (30-year fixed)Property 2: >$70k in EquityValue: $325kDebt: $252k @ 3.38% (30-year fixed)Extra considerations: - I have $15-20k liquid to use for any of these deals- My current job is relatively stable, but not high-payin- Current properties in TX, living in NY, looking to invest in Mid-West (crazy, I know)- No other debt obligations besides the two mortgagesUltimate goal/timeline: Though a bit ambitious, I’d love to build up the portfolio to 10-20 units in the next two yearsI understand that any/all replies aren't financial advice; all ideas welcome for information purposes. 

They taught me how to professionally engage the brokers and sellers and submit all-cash offers using THEIR cash. 

90% is pretty high.

If you really like the place but you feel that it is priced too high for your budget, instead of saying “it’s priced too high” and insulting the seller, simply say “I absolutely love your place; it is exactly what I want, and I’d really like to buy it.

If so, how do you trust you're getting a quality tenant that is safe?

I'd keep 70% as a base and shoot for 90%+ on the high end.I think I'd be pretty happy with 90%.