We knew the boilers might be a hassle going in, so the plan is to add gas furnaces and central a/c as the boilers age out, so even if this is a typical expense each fall, it hopefully won't last forever. 

Also keep in mind that in Illinois, typically attorneys handle title clearance so they are very involved with the process. 

The biggest tip I can think of : make sure you find a realtor who specializes in working with investors, typically they will have investment properties of their own.

Typically, Owner-Occupiers can get low interest, low deposit 30yr mortgages even for a 4-plex, so a fully occupied scenario is not what they want!

Anyone using something new other than the typical sites?

Also, do you typically give your number out to the neighbors of where you have your home for such instances? 

That is not how it typically works in most places.  

When you hire a buyers agent typically you will technically agree to paying them.

Do plumbers typically do that?

They do both pre-foreclosure sales (typically on the courthouse steps) and bank owned sales (typically online auctions).