I would find a good handyman to address these in batches which will save you money.Tell them cosmetic issues will be differed up to 60 days to slow them down on creating new lists.Tell them their constant repair requests will play in to your decision at lease renewal time and rent increase decision time.

I have not yet seen the property in person but it looks like it will only require minor cosmetic repairs (paint, flooring, trim, cleaning).

I’d rather have an empty lot.There are enough cosmetic rehabs (sometimes including roof, windows, siding) out there that I don’t get involved with huge rehabs like this that could tie up me and my cash for far too long. 

I'd like to expand and market this LLC to offer management services that include leasing, accounting, capital projects, routine maintenance management, etc...Am I required by law (Illinois law) to collect management fees through a sponsoring broker?

Just because you don't see auditors knocking down doors of those that abuse these guidelines on a routine basis, it doesn't mean it doesn't happen.

This house had good bones and needed a lot of cosmetic work.

My plan is to live in it for a year or two, make cosmetic updates, add a bathroom and some square footage down the line, and then either 1) rent and refinance or 2) flip and invest in something a little bigger.

Imagine with me, that your workday began with the usual routine, but halfway through your morning, you received the news you’d been laid off.For most Americans, that means zero income starting tomorrow morning.Now, let’s pretend that during your employment, you leveraged your money.The rich don’t work for money.

We are doing some minor cosmetics to really make the home pop. 

Essentially a move-in-ready place that has room for cosmetic upgrades.