They have all appreciated at the same percentage rate as the surrounding houses. 

The thing I am having the most trouble with is knowing what numbers and percentages to put in for certain things. 

(assuming I put forth a good percentage for expenses, and my own cashflow as well)  is the brrrr calculator always accurate???

I've checked and this works out for everything.You will need these accounts and name them as such or you might get confused:Airbnb - bank:  bank accountAirbnb - fees:  expense accountAirbnb - vendor:  set up under vendor Airbnb - customer: set up under customerSales tax item and percentage your city chargesCity where you pay sales tax set up as a vendorFigure out the taxes by backing them back out and do a sales receipt for the rental and the cleaning.  

Look specifically at the year-over-year Reserve Contribution percentage increase rate which should be near or slightly above inflation (i.e. 3-5% per year).

If so .. what would be a good percentage?

Never the less, I admit that in percentage terms (versus using dollars) Cleveland may have better cash flow over the last 10 year holding period, but the higher appreciation market, by the fact that it is a high appreciation market, will catch the lower appreciation market given enough time even in percentage terms. 

This in effect reduces my investment amount which increase the return as a percentage of investment for any appreciation. 

Of course they will make a percentage on top of the money they borrowed.

What do you think about giving him a percentage of the overall property?