Check on VRBO/AIR and see what your competition is offering.

I use my annual bonus checks from my full time job and stock rewards to provide cash to finance my property investments. 

My initial thoughts are to check with an attorney and CPA that specializes in the and can give you feedback on your specific situation.

"Payment for properties must be in the form of lawful money of the United States, a certified or cashier's check from a Pennsylvania Bank"3) How the heck am I supposed to know the amount to have my cashiers or certified check for if I dont know the final sale price ahead of time?

So, you would need to search for each owner in the title chain to check that. 2.

Hey Rafal, since you're looking to invest in the Midwest market my recommendation is for you to check Ohio. 

Require background checks on all adults living in the house.

I did most of the book-keeping myself but used the CPA's to file taxes and double check my work. 

I would also double check the city building department since (if I am reading correctly) you have two income producing units on this property.

Next, check yourself...are you living your life the way you have ranked them?