What difficulties or unexpected issues did you encounter?

I was in sticker shock but I really need these repairs done.

As you get over 4 units you need to consider not only how you would evaluate the property as an investment but also how a commercial lender will evaluate it.Things that you might look at that you might not consider on a SFH are cap rate, Debt coverage ratio, various way to calculate ROI, and expense like snow and trash removal that you don't encounter on SFH.

The sticker prices are pretty universal I'll just pay the sticker price. 

Because it takes repetition for people to remember things and you have to be top-of-mind when they encounter a potential client for you!

@Nick Littleton personally, I have not encountered this issue (I've done numerous owner occupant mortgages, refis, and HELOCs, and no lender has ever asked me about my property management experience, or whether I'm using a PM, or anything about how the property is managed...other than asking to see signed leases that correspond with the rent income I reported on my taxes), so I was surprised by what you described......I'm interested to hear from the lending pros on here: is property management or property management experience a commonly used criterion for loan qualification? 

Calumet City is now going back to enforcing having the rental license sticker in the window and Markham will give $500.00 fines to any work truck in front of your property that isnt registered with the city. 

What are the unforeseen challenges that you have encountered ?

Looking to see if others have encountered this situation before.

Honestly, no sump pump could have withstood the amount of water many Chicago basements encountered that day.