I'm working with condos, and yes the HOA's can be a pain sometimes but the one upside is that there's no exterior maintenance, no roof to worry about, and most of the time I can call the building management first if there is an issue.  

I was actually looking to see different opinions on buying with tenants as opposed to without tenants. 

Back to the topic - I'm presuming an option to buy contract (as opposed to a P&S Agreement) would bring about even more issues in IL?

All of my properties are SFH and would not be opposed to getting some smaller multi family soon.

Yet on the bad side they have the law on their side and if they wanted to they could make life quite hard for any opposers.

But if its already pealing can I scrap exterior paint myself or is that going to violate EPA regs?

Vacant land, however, cannot have a homestead classification and I was able to get this changed so I could sell the property in 180 days as opposed to two years.

I might have to go north to find deals, I'm no opposed to that but local would be better.

The agent tells the seller "hey I can get you 70k and I will keep the rest as my commission" This is the same thing as an agent signing a contract to buy a house for 70k knowing they can "flip" the paper for 100k as opposed to telling the seller to list it for 100k with the agent taking a commission of 6 or 7% or whatever % is typical for the area.

While I wouldn't be opposed to just buying, I would prefer to also live in one of the units.