If I've misunderstood and she's just a person w a lot stuff, could be workable. 

I've looked at multifamily on MLS on and off for a year and have only seen a couple deals that might be workable if you get it at discount and have the resources to do a full reno.

-Sort your Master List by your desired qualifier (address, property owner, whatever).Now, you can see which properties are 'tagged' under multiple categories.Assuming you get your data in similar formats, that should be pretty workable (and free if you have excel).Now, if you're working with a mountain of data, and the formatting is wildly different, this probably won't work for you. 

The HELOC and credit cards now, and refinance once renovation is completed, is workable, as long as you don't get your DTI too high.  

STR regs are definitely a complicated thing to get your head around here, but generally are workable. 

I am hoping that someone else will have info on how to do this because, to me, it just doesn't seem workable.  

Not as good as the real thing, but may still be workable in your situation.4.

If Chicago winters are as bad as one here's the amount of construction work able to be completed will also diminish.  

Yes, it looks like a workable deal.

Additionally, with your available cash, you could possibly buy more than one LTR property as long as the leverage is workable.