It takes a few buildings to cut your teeth, but it's worth it and can really open up inventory in a tight market that we're in (for 2-4's in Chicago at least). 

If your buyer is using cash, there shouldn't be any problems whatsoever.

I only have about 10k in there so far though, and the market is starting to move sideways in terms of stocks, so Ill have to grit my teeth and put in some extra hours for that down payment.

I think you're officially in Phase 2 --Pase 1: earn your degree in the real estate school of hard knocks, occasionally getting your teeth kicked in.Pase 2: Become successful and get tired of the same day to day nuances.

Housing supply is never going to catch up with demand without huge government incentives or intervention, because there's no financial incentive to build housing for sale, much less for rent, in the slots most desperately needed (sub 200k); the cost of labor and materials makes low-income housing construction make no financial sense whatsoever. 

@Tom LundbergIf you join the sk landlord assc (a completely useless organization, literally serving no purpose whatsoever) you can raise rents 2x annually.

Hes not telling people to buy or not buy in any areas whatsoever.

I call my property management company frequently and they keep saying "we are in the process of sending a vendor out"....Even getting an estimate for the repairs is like pulling teeth.  

So there is a lot to sink your teeth into depending on your style and what properties you are looking for.

I don't think I've ever seen a Lease that says they Won't/ Can't  (That would be suspect to anyone with any savvy whatsoever, incl.