I have seen a three units in Cicero trade for that kind of money, and they would cash flow very well.

If YOU were the homeowner getting that kind of news, you would have to wait until Monday to get it fixed! 

It is probably a good idea to look at one of each kind, so you can tell them apart while shopping.If you think that any of the windows have been leaking (often around the bottom), you might be prepared to replace rotten framing after you take the old window out. 

I just want to make sure that it is absolutely necessary to obtain both kinds of insurances. 

I kind of jammed through it.  

Once you're deemed credit worthy by lenders you can start using leverage which needs to be used VERY carefully but is also extremely powerful.I personally do NOT recommend that someone with a trades or self employment 'life track' as you are describing is best suited to buy a first house with cash, and for instance use your time to fix it up.Few reasons here:Firstly, often the kinds of 'cash deals' available are ones that can to generalize tend to be more cash flow type properties (as opposed to equity properties). 

I've never bought in that market but have family there and still love to visit. 

Use conventional financing to buy each 4-plex individually, but close them simultaneously.It is likely that the owner doesn't care what kind of financing you get, but their loan might be a tied loan, so untying them becomes more complicated. 

I would not skim coat it for the reasons listed above, and even if it wouldn't delaminate, best case scenario, it's still going to look kind of weird. 

Please advice me on which markets and what kind of properties should I be loving for.