I'd have concerns of buying high, then moving back home or to family or to next job and being underwater when I wanted to sell my house and losing a lot.

It's the best for everyone concerned. 

What lender is saying Or is concerned is that you may have ordinary income on box 1, but if you never took it out, how can they be sure they you have access to that cash.

Thank you Rick, actually my concern is whether a 5 plex would be ideal or to convert it into a 4 o 3 plex, my feeling is that there is room to move walls and do major changes.

Today to develop these are the concerns: is there water available; is the plan similar/compatible with neighbors; parking; traffic; time frame; cost....  

The biggest concern I would have is what happens after four years if he wants to stay but doesn’t want to increase rent.

My main concern is the cost to furnish the homes is something I’m not sure I want to spend on.

Here is what I’m concerned about, i did all the work myself/ paid cash to get it done.Here are the upgrades(I’m sure some of these might not need a permit but I’m new So idk)-Added central heating and air -tore down two walls to make an open living concept (non load bearing)-renovated kitchen/moved gas line-replaced some of the foundation 2x6 floods became they where damaged by termites -add/move electrical sockets-new floating floor-replace pluming with pex/ pbc-painted inside-replaced a window- maybe more but you get the big picture.Will the appraiser report me to the city?

It made me concerned about the agents due diligence on the others.

The cashflow is decent as a midwest city, and there are some really nice suburbs as well.I'm mostly concerned with the future of Chicago, and if it will continue losing population, or if things are expected to reverse/ level out over time.