But, if a slightly different, even related problem happens even the next day. 

Banks decline people that are self-employed, not because their tax returns are too complicated, but because they take massive deductions (legal, I know) which reduces their adjusted gross income.Incidentally, banks turn down W2 borrowers that take massive deductions for business related expenses which also reduces their adjusted gross income.I would suggest you look on BP to find an investor friendly local lender that you can sit down and have a coffee with. 

This jist of the rules are no mixing with disqualified parties, which essentially mean linear relatives: parents, grand parents, kids, kids in law, grand kids.

Looking to purchase tax liens in cook county.  Would like to know the approximate fees attorneys charge to file the Sce 22-5 Notice and then the cost to obtain order for tax deed.  Any referrals for attorneys would be...

as your primary you should be able to get an O/O HELOC my guess on the move out question would be dont ask dont tell, so residential HELOC's tend to be 10 year term, so I would maybe get the HELOC from a bank you dont do investing related banking with maybe an out of area bank or bigger institution. and set up a P.O. box or a different address to get correspondence from them (totally reasonable in a multifamily) this way when you move that doesnt change, so no red flag for them to call it due.

If not, those are relatively cheap in the grand scheme of things (the value they bring to your unit.)

And I’m sure other groups related to them use it as well 

I am already aware of the city's health department requirements of property registration.

Has anybody dealt with cherry oaks or any type of tree-related problems before?

I'm relatively young (31) but have learned a lot from my Grandfather in terms of real estate before he passed away a few years back.