When I sell 2027, Should I pay capital gain tax for entire 500,000 or pay partial capital gain tax (500,000 - 200,000= 300,000) for only when the home is being used rental (2022 Feb - 2027) Your primary residence will qualify for $250k ($500k if Married) gain exclusion if all following requirements are met: You owned a home and used it as your main home during at least 2 of the last 5 years before the date of the sale.You did not claim any exclusion during the last 2 years.You did not acquire the house with a Like-Kind exchange during the last five years.

I have plenty of friends that are realtors, but I am trying to hold on to as much of the funds as I can to be able to dump them into the Taproom/Pizzeria Project (I have already acquired this new property and am ready to build out).

Awesome story of your grandfather's grit to acquire this multi-generational wealth for you all.Honestly, commercial loans are scary. 

I have an opportunity to acquire a 4/2 house with a second lot that has 4 tenant owned trailer lots for $200 each (which could be raised).

One of the main reasons I am saying this is many of them have significant title defects that can be remedied but will also take significant time, effort and cost.For example I was reviewing a performing 2nd mortgage recently but the mortgage did not include the legal description and metes and bounds as required by the county.

Given your goal for cash flow to supplement self-employment income, I'm guessing acquiring more doors? 

I will really appreciate some replies to this post as I am trying to acquire my first two properties and need this paperwork to get started. 

@Heidi M.This is a non-tax related thing to consider as you lose 10%-15% in value when you sell a home and acquire another home.What is missing in the current home that you are looking to get a new home?

What upgrades brings a higher appraisal (I know there are other factors like comps).This is for a BRRRR property that's rented but recently acquired and still had halogen bulbs and brass fixtures, just to give an example.

I recently sold my home in August 2021 in which I used an FHA loan to acquire in 2020.