@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

Your realtor should be the first source of guidance.For anyone here to provide you some guidance, you have to be more specific on the ask.There are always many things to consider when planning for different strategies.

Ultimately, a do a little bit of everything in the residential space depending on the deal I find, but either flip paper (wholesale), flip houses (remodels) or flip the debt (buy and holds).I am looking to connect with as many of you as I possibly can while adding just as much as value wherever I can! 

Hey @Nike Onyechi - Not sure...but maybe it was @Tom Shallcross who was on the podcast somewhat recently, a value add investor, and chicago broker.

Personal money How did you add value to the deal?

So, I am indeed getting monthly payment from my buyer that would cover both monthly mortgage payments and also provides me interest only payments on the difference between the sale price and mortgage payment. 

Prices a few years ago were based on expectations of (in addition to interest rates staying low): - Then current operating cost assumptions (like insurance cost expectations being flat)- A seeming disregard for record levels of new inventory / supply hitting the market- Extremely high inbound migration expectations which are likely to not be met, due to both natural disasters and the boomerang effect when people from California or the Northeast move to the American South and hate every minute of the humidity, the large and relentless swarm of insects, and the occasional hurricane. 

There are a lot of high character folks who get sucked into garbage Co-GP style guru programs.

Being a real estate professional allows you to treat the income as non-passive, allowing higher high income tax payers to pay less in taxes.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.