I'm currently in the Lafayette, La market interested in learning more about analyzing deals with a buy and hold mindset. 

Whatever extra cash is available would be the cash out.So, for example, if you have an $80,000 loan on the property and the loan fees add to $2000 then:$175,000 * 0.8 = $140,000 loan$140,000 new loan - $80,000 paid off loan - $2000 loan fees = $58,000 cash out

I currently own six properties in Indiana and I'm now looking to buy a condo here in Chicago for personal residence.

Buy busses and airplanes 

is buying more. 

We currently live out of state, so we had to tack on extra days to our visit along with extra hotel expenses in order to make sure everything was fixed.

I used myself as the buying and selling agent

Partly for the strong casflow that we enjoy after 30+ years investing along with other reasons.I would probably not buy additional property all cash, but improvements and betterments will be paid in cash or at least quickly.Leverage is a great tool when used properly. 

If they don't charge, then they won't have any incentive to take care of these repairs with urgency, as it would be extra work that they have to do without compensation. 

I was looking at these areas as well as they were cheaper than buying in Rockville and also appeared to have some decent homes.If getting the ADU would be tough in general and renting by the unit in those areas would also be challenging I may need to rethink my strategy.I am doing this as a first time MD homebuyer and looking at my options to rent a portion of the home.