Would like to hear how others handle optional renovations during tenant vacations and if they apply rent abatement for any loss of use.Backstory: Renting out a basement apartment with painted concrete walls.

I was wondering if anyone had any tips, suggestions, or otherwise useful info I could apply towards my goals. 

I have an individual interested in applying for a vacant townhome I own, but is asking whether or not a bankruptcy filing will be an automatic 'no' for the application.

A tax known as UBTI with federal rates of 37% may apply if this type of transaction is done with any frequency.I would encourage you to look into crowdfunds or private lending from the IRA, as those are most suitable for your situation / capital amount. 

So most hands-off and absentee landlords just keep on trying to maintain these out-of-date systems well beyond their natural service life.

AlSO, avoid companies that require money up front just to apply.

Since your husband is 59.5, early distribution penalties wouldn't apply, but taxation still would.

When you apply for financing, the lender is going to dive into your finances and still require you be able to cover ~6 months of costs (held in a liquid asset), and may not count the rent generated from the other units. 

One benefit I have seen to a HELOC is that you can set your direct deposit up to deposit into the HELOC and use it as your checking account perse, and naturally, you can pay off more, and faster.

But also this is the nature of Chicago.