Perform proper tenant screening if they will be living next to your family.

I would say its tougher these days to find easy flips in the multifamily space, but if you are looking to buy/hold for rental income you can cash flow about $1000/mo (after debt service) on a $500,000 building (4-6 flat) in several areas.  

*It's easy to get into the driveway when the house is on the left side of the road.  

Is this a good criteria to have or is there an easy way to handle the lead paint situation?

Aside from aesthetics and possible trouble with wind blowing the door, I've read that this is a security issue because, in the absence of special hinges, it's easy for a burglar to enter the home by removing the hinge pins.

Assuming a mortgage is not a Sub2.Sub2 or taking title subject-to refers to taking over legal title to the property subject to the current financing, encumbrances, liens, etc.If the prior owner is now a leasee, hopefully you structured that well and setup and fund a new tenancy as soon as title transfers over to you so that the rights and duties of both parties were clearly laid out.If they arent in a contract any more you can give them a notice to vacate and the proper time to leave depending the local tenant landlord laws in your area.

In most areas of the country, a properly priced duplex will never make it to the extended period Set up a search at Hud homestore and you will be notified once the property hits the market 

The idea of allowing a tenant to paint any surface in my apartments is just crazy -- they'll screw up everything I've done to bulletproof the paint jobs and allow easy touchup and colormatching.

I've heard of IL strict deposit return protocol so either way give proper notice of intent to withhold in a timely manner.I withhold the days of rent it took to re-rent when I receive no notice. 

Chances are you will still have to put your own capital into the deal, but this method, if done properly, can minimize the amount of capital required.