Most importantly…do you have someone in your corner looking over your shoulder and giving you solid advice on a regular basis?

The potential is still there, and in an owner occupancy scenario rather than putting $800 extra into your rent account every month it is shouldering the burden of your housing cost.So, to evaluate your property, add up your total costs as mentioned above and then divide one months total market rent potential by that amount.  

This allows the driver to have the next unit on their left shoulder or mirror. 

I had time to prove myself.But there is something to be said for bonding time when the suit or tenant is with you shoulder to shoulder pushing your car to jump start it on your way out...

There are lots of air-2-air heat pumps much further north than Chicago which work just fine - solo through the shoulder seasons and with an ancillary heating source in the dead of winter.  

I would then tell him that I think I have a good deal, but need someone with experience to look over my shoulder.  

STNL you have a long term lease in place and the tenants shoulder increasing costs and no matter if economy is going up,down, sideways you are getting XX percent each year increase.No asset class is perfect.

If you're at ground zero and you want to get into some bigger deals, you simply must bring some sort of value to the table.Listen to how @Joe Fairless explains it here:Standing On The Shoulders Of Giants

There have been a few bumps in the road but thankfully I have an excellent property management team who has lifted a lot of burden off my shoulders. 

Or bring in a partner or consultant who can look over your shoulder.