Take a look at the various due on sale clause articles on BP. 

Agreed per usual, macroeconomic forces that most people discuss by reading the news, interest rates, or "good time" require such large amounts of capital, like $500m invested, or $1 billion into certain regions.Everyone else will make money on a specific asset.

A lot of forum members are very knowledgeable in their respective fields related to real estate investing.There are some pretty nice discounts on many products and services offered as Perks to BP members that you might want to check out: https://www.biggerpockets.com/perks/proIf you haven’t been to it already, the Bigger Pockets blog features links to their fantastic podcast and many great articles: https://www.biggerpockets.com/renewsblog/

I stumbled upon this article, written by a tax attorney, in a respected tax magazine https://www.thetaxadviser.com/...It implies that the 3-yr window on amending your tax returns and claiming a refund starts on the day you actually filed your initial return and NOT on the extended due date.

https://www.kxan.com/news/loca...

I’ve read articles and watched a few videos but I’m still confused on the general process. 

I have been listening to podcasts just about every day and reading multiple blogs and articles a week. 

If she can't find one, expect some drama (staying beyond the lease) and possibly an eviction.You might want to (seem to) "Side with her" when you break the news to her, and tell her that there are "Long Term" Motel's that don't ask many questions who MIGHT house her and MR., and that you are sorry but that's the way it is.And BE SAFE, you don't want to be the reason (victim) Mr.

This third party could be an agent, attorney, financial advisor, or any person that's going to be ok with giving you bad news.

I found this article that may help you :Chicago RegulationsI've considered doing some STRs in Chicago or suburbs since I'm originally from there.