The rental home has a mortgage balance of $111,000 if that plays a role in your answer. I expect my capital gains taxes to be north of $30,000 from the sale but I’m not really sure how to calculate what it will end up being.

Maybe to gain more freedom at that point you could transition to more of a consulting role so you wouldn't have to have a set schedule.  

Here, they get transferred to the tax roles or you can work out a payment plan. 

Would like to find a hungry agent, who's going to role up their sleeves and market and sell the property.Willing to sell direct, if a buyer came direct. 

Any suggestions for full time roles and where to look?

We work in Chicicagland generally speaking but location and scope have a big role in determining where we can work?

The goal is to have done some DD on the top property and have PSA signed before locking in 3 choices so at that point other 2 are just fillers.So when my client is selling their property I often try to see if they put a clause in there where after buyer goes hard with EM purchasing their property the seller at their discretion can exercise an additional 30 day extension before they close to start the 45 day ID period.The NNN properties get multiple offers sometimes dozens of offers the demand is so strong.

I would try to figure out what kind of work you enjoy doing most and pick a role in real estate that aligns with that most, or try a few different roles to get a better idea of what you prefer. 

If you can better protect and grow your retirement savings placing the plan into investments such as rental properties or private lending, great.The plan could purchase a property and execute a BRRRR, but your role is limited to being a "fund manager" and making sure the contracts are signed, vendors paid, etc. 

I would love to meet up with individuals who are open to doing role play scripts for seller calls, and practicing running comps.