At the time, I was married, thinking we’d have more kids, and maybe move my dad in as he ages.Well since then, I’ve gotten divorced, decided I’m one and done on kids, and switched jobs to have a longer commute.

Not married to NoVa but just a thought, I want to get tapped in a local network (DMV) for mentorship and h]guidance.

Well... it turns out married life may not be married life by the end of 2023.  

What I mean is, it looks like as a married couple filing jointly we pay $0 in cap gains on first $94k, so could we use a strategy to pull out $94k in cap gains then 1031 the rest?

I started when I was married with 2 kids, and a full-time job, It was not easy when you have others who depend on you, and I was living paycheck to paycheckYou have time, so take advantage now if we can

Before that it was primary residence since January 2019.Do I need to sell it this October to avoid capital gains tax to qualify for 2 of last 5 years exemption for capital gains (up to 250K single, 500K married filing jointly)?

When I move out in Sept, get married, and fill my current room, I'll basically be breaking even after expenses and maintenance.

If married, that would be a $1.5 million writeoff against your overall gains.  

I understand your apprehension about rates, but as the old adage goes you "marry the property but date the rate".

The filing is a public record and when you file put maiden married etc. names DBA crazies.