So, I'll soon be moving to Indianapolis and I want to buy a decent house with the intent to air b&b the extra space.

Two things:1) You won't be able to live in the property if you get a hard money loan for it.2) Even if you aren't planning to live in it until after refinancing a hard money lender may still be hesitant to provide you a loan in the event that you may have difficulty refinancing out of their loan.

@Kristin Feerst I think you are going to have difficulty purchasing the property wholesale as you will likely need hard money for the purchase plus $40-$80k on average to fix them up.

Purchase price: $338,000 Cash invested: $338,000 Purchased home for myself rented out extra rooms to offset costs.

@Kevin Moyer - I do have rentals in Philadelphia, and yes there are lots of extra things you need in Philadelphia.

I am having extreme difficulty figuring things out when analyzing the market. 

Plumber thought that since the carpenter kept telling him to do things he was maybe my husband or boyfriend and that he had the authority to agree to me paying for these extra things.  

Legally the late fee has to equal actual costs to landlord, so you have to be careful not to charge too much.I make it clear to tenants that while the state may give them an extra 5 days to put the check in the mail, rent is actually due on the 1st.

Is there any extra land their that would bring in more income and possibly more tenants (like farming or storage)?

Will they cost you any extra funds?