Im active duty military, and am planning on selling one of my homes (Property #1) in the next several months, which meets the 2/5 capital gains tax exclusion criteria of having both owned and lived in it for 2 of the last 5 years prior to selling (and my understanding is that the rule actually extends to 15 years for the military).

I have 100k+ in equity in one of my rental properties but due to the pandemic my income suffered quite a bit.

Not saying you would, but someone in your shoes could easily walk away if the project got tough or went south and potentially end up suffering no loss. 

The company I used was pretty bad with communication and I had to extend the close on the house twice because the refi wasn't done on time.

So, the only way to answer that question is to do a rather involved analysis or suffer a loss (not recommended (-: ) In the event of the loss, you would get the value of each element at it's current remaining life-- ex. suppose flooring is a 20-year component and it's 10 years old, you would get 50%.

I believe he will extend the order for probably a few more months near the end of Dec 2020, and then again after that in 2021. 

That further means you may have to suffer the financial repercussion that comes with not taking care of your partner.Unless, you are ready to incur the CG(Capital gain)  taxes takes that comes with a property sale, I suggest (not strongly) that you rent to your neighbor, make sure you have all legal documents in place, most importantly let them understand that you are working with a partner . 

The STRs in urban cores have suffered much more than traditional vacation destinations. 

I wonder if “gold bugs” are going around quoting JP Morgan saying “gold will suffer for years because of Bitcoin” somehow I doubt it.  

@Victoria Amador You could renegotiate the terms on the seller financing (extend out the term with a temporary forbearance, or change the payment schedule to an escalating payment schedule, etc.)?