You get a Capitalization Rate (CAP Rate), which equals your annualized return by dividing the Net Operating Income (you had gross in your narrative) by the purchase price.

Obviously if I intend to have a top performing STR in this market, my buy box will allow for a much higher max purchase price, but I wouldn't feel comfortable with shooting for the max if there aren't clear ways to beat these competing properties.

People out here are bidding over asking price to cash flow 100 bucks a month on a 150k investment. 

The buyer agreed to cover the cost of the new appraisal, which came in significantly above the purchase price.

Here’s the situation:Purchase Price: $540,000Down Payment: 20%Mortgage Rate: 7.125% (30-year fixed)Monthly Expenses (Mortgage, HOA, Taxes, Insurance): $3,706Realistic Max Rent: $3,000As you can see, I’m currently short $706/month even with max rent.

I find properties on the mls and send them to the agent with the offer price.

Do you have any idea of the price point you can afford and are you looking for turn-key properties or something along the lines of a "fixer upper"?

Purchase price: $376,613 Moved to Orange Park, Florida, from Delaware three years ago, choosing this home as the perfect place to settle and grow.

Meaning that the number of showings show you have it priced well? 

Purchase price: $500,000 Cash invested: $100,000 AirBNB in West Sacramento