Bryan, it sounds like you want to have your cake and eat it too.If this were possible --- and I am not saying it is or is not possible --- my guess is that a lender would say that the monthly rent payments that you collect could stop anytime and thus making a loan with that stream of payments is extremely risky.

Taxes and insurance alone would eat up $100 per month around here for a 20k house.

They will just be concerned that this are places to eat, shop and do it safely.

Did the right thing when opening the walls but lost the eat-in kitchen.

Was eating breakfast with my sister at Sambos and asked the usual waitress question anyone mention maybe buying or selling a house this week?

These expenses add up very quickly and can eat into your margin very quickly.

I thought of partnering with family, but then thought of how much it would eat into my profit.

(There are apple trees on the farm, LOL)If you don't eat you'll die.

If you have 100k equity in a house but it's not going to be easy to rent (same number of bedrooms (3) as a smaller house but bigger sf by 1000) do you sell it and acquire a smaller house that's more "rentable" or simply lower the rent price and eat the greater maintnance costs (carpet, two AC units, etc)?

You are probably working with folks that can eat your lunch and send you packing.