They did request a late check out but we declined so maybe that bothered them idk.

For Insurance you could bother your insurance agent, but approximating them will be fine.., maybe you could use numbers from your own portfolio for similar homes, or you could use mine, which would be like $800 for the cheap one, $1,500 on the mid price, and $2,200 for the biggest ones.  

Usually I get a few good applicants and don’t need to bother them again.

"If something is bothering you, and you can do something about it then do not worry about it. 

State #1 - no state taxState #2 - your home stateState #3 - state that allows a composite return, you opted inState #4 - state that allows a composite return, you opted OUTState #5 - state allows a composite return, but the sponsor does NOT offer themState #6 - state that DOES NOT allow a composite returnYou will receive a Federal (IRS) K1 plus five state K1s, for states #2-6 (no K1 for state #1, since it does not have state-level tax)State #1 - no issueState #2 - you do NOT want a composite tax return for your home state, since you must file you home state tax return anyway, and composite will mess it upState #3 - no issue, they will take care of your state exposureSo the problem is states #4-6: either no composite returns allowed, or the sponsor does not bother with them, or you choose to opt out.

Regarding your naivity about whether to evaluate one or two units for cashflow, did you bother to factor in what you would have to pay in rent if you did NOT live in one of the units?

It bothered me at first but then faded.

I've had them on the advice of an attorney (They will always say to get one:-) but after research I don't bother anymore.

I hate bothering you, but…”- “I haven’t been able to get ahold of you.

Why bother with Chicago with exorbitnt property taxes there.. if you move simply sell, that's it.