I personally take pictures of my receipts, email them to myself, save the receipt in google drive and upload in it in Stessa (charges can feed into the system automatically).

After they book your place, and in the automatic booking email, I would again mention the above comment just in case the prospective STR tenant missed it. 

I am imagining the most important factor is the neighborhood where the property is situated, but does that mean a recent sale from 2 miles north will automatically override a similar property/sale from 5 streets away in the other neighborhood, or will both of them be considered?

If they aren't notified in writing of approval or denial within this time frame, the lease will automatically go into effect (regardless of your own screening process).Hope that helps!

I live and invest in the West Allis market. 1 Beds are not an automatic drawback IMO......I've seen people stay for YEARS in 1 bed units. 

Ask your tenants if they want to sign another 2-year lease but this time add in the $50 discount as a 2-year offer only and clearly state month-25's rent indicating an automatic increase of $50.Lastly, I'm sure you mean no mal intent but be aware of your Asian descent comment. 

There’s the annual inspection which is automatic every year at about the same time.

On another note, I have heard taking rent via a bank deposit or Zelle is not the best way to accept rent because it automatically goes in.

Run your numbers based on lot rent alone and add a separate value for homes, but only if they're newer and in good condition.Just because someone is willing to seller finance does not automatically mean a great opportunity for you.

If you change that you will have 55 bookings intead of 50, the cost of your cleanings should automatically increase for example), keep playing with the models until you find one that looks reasonable.Hope that helps!