Timing of Sale (vs Rent)

[Sean Craigg]

I have a primary residence (for 2 years) and then rented out (for 1.5 years) and lease renewal is coming up at the end of July.

Tenants want to extend another year for a higher rate but I want to sell it before the cap gain exclusion (121) expires.

I want to ensure the house is vacant so I have a month to prep before selling it in Spring of 2024. Which month is the best month to sell?

Then I can determine the lease end date. 

Do you think after the 2020-2021 increase, there will be another increase on the horizon in the Round Rock area in the foreseeable future? Would it be worth keeping it as a rental long-term?

It's a (>4k sqft) SFH at a top school district.

Regarding the cap gains exclusion (121) - is the 5 year period back-calculated based on the date of the final sale? And 2- years primary residence period based on your physical presence (and no documents?)

Thank you in advance!