If they insist on being there when the work is being done, they need to arrange their schedules to allow that.I gather Chicago is a pretty tenant friendly area. 

If they insist on being paid, negotiate.

prepare for an age old debate on this forum.you can't get good residential mortgages for an LLC my opinion is to move the home into your personal residence and get the good financing, the liability is negligible. if you insist on keeping it in the LLC name, you'll have move it to your personal name, get the good mortgage, then quit claim it back to your LLC.

We learn  from our realtor; one of her client try to request current owner responsible to deliver with vacant upon closing;  however, owner insist only responsible to issue notice to the existing tenant.

Any of my clients who insist on buying in Toronto, or the "tighter GTA", do it because they have experienced market downturns, and know that, usually, where there are the most people, the most money, and the most job, weathers the storm better than areas which are further out.

Our main policy covers us (so long as we don't allow STRs, which we do not), so it's been something I've been lax about.However...One of our tenants actually read the lease and got the policy without my insisting, and she went with Lemonade Insurance. 

He than asked what I would offer, I tried to dodge it since he was obviously not motivated, but since he insisted I told him...20 to 25k. 

We tell the housing office that we will keep advertising it until we have a signed lease, which they won't authorize until after the inspection. 2) They always insist on lower than market rate rent, which we won't accept, even though the federal guideline tables provide for more generous rents.

Third time because they insisted that I needed to have a separate EIN for my LLC.

I see you are in Sisters Oregon I'm sure you've enjoyed the market!