Some of the national data sites have pricing suggestions that run both high and low.

All my experiences on Booking.com have been good people at high profit.

I see a lot of awesome amenity packed outdoor hang out spaces with outdoor pools posted on the many STR related social media accounts that I follow, but I don't really ever see any pool fences or other safety features highlighted. 

If you care just about positive cash flow (and you don't care about population growth, macroeconomics, or appreciation), definitely go with Cleveland.

Getting a property with a partner / friend will not help you from getting hosed on taxes.I wouldn't move forward - You mentioned beng a high income earner so your hourly rate is very high.

I was definitely on the fence about this one for a little while before making the purchase, but there were a number of attractive features that ultimately led me to move forward with the purchase.

I looked at their booking calendar one time and thought it was pretty empty.I guess you don't know until you try...and probably depends on if you want high occupancy or high rate?

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Both platforms have a feature that shows monthly transaction details, giving you insight into each booking and its corresponding rate.

So, start saving now while you are in High School.