My peace of mind is worth something, but I'd like to put those multiple thousands of dollars into my new place instead of this old house that I'll be leaving behind in the not-too-distant future, especially since I won't be fixing it up.

The couple is MFJ and qualify for the $500K exclusion which leaves a net LTCG of $700K ($1.2M - $500K).

This leaves the option of paying the original amount if things get tight for one or two months.

At least that is my understanding.Do I simply raise the rent enough to make her want to leave, but not an outrageous amount?

My mother would ask me if she should leave my step dad.

Our contractor is being sued leaving us in need.  

So, I have to contend with leaves & sticks cleanup in the gutters also.

I assume you have intentions on making in liveable, so if the city sees work being done, I’m sure they’ll leave you alone. 

Let CPA know about categorization so return can take the deduction for the correct properties.May or may not want to shuffle which entities hold what....may inclination is "if ain't broken, don't fix it" and leave entities "as is".....Between QB and return, can distinguish what is a T/B and what is not.

Her maternity leave pay will end soon so it’s either go back to a J.O.B. or have her more involved in the business.