We have worked with Investors and they are never really married to their Realtors unless you happen to connect with somebody looking to do a long-term hold and actively trying to find a good realistic deal. 

My brother currently lives in Dallas and pays an arm and a leg to rent an apartment (He is married so cant house hack).

Convert the Property to a Primary Residence: If you live in the property for at least two of the five years before selling, you may qualify for the primary residence exclusion, which allows you to exclude up to $250,000 of capital gains ($500,000 for married couples) from taxation.4.

Meeting that 2 in 5 of the last requirement allows a single owner to shield $250k of appreciation and a married couple to shield $500k.Unless you predict a lot of income from the MTR or you feel that there is a lot of appreciation incoming over the next three years (minus time get the property sold), you may want to consider collecting your $100k (passing GO) and redeploying that money to whatever you feel is its best use. 

(I am usually lazy about courses and pick + choose my engagement) This feels very different from most things I have "tried" to work on in life (except for when I turned to RSD and Owen Cook a out 13 years ago to improve my dating life which resulted in finding/ attracting and marrying the girl of my dreams!

I am getting married next October and want to be able to hang out with my future children but it is a little hard to visualize that since I don't have kids and am not married yet.What book would you recommend to read next to really pound my why into my head?

Other items such as having accounts in a foreign country.If you are single/married, with a few W-2's, interest/dividend accounts with one rental property.

Here's the drama part, while married her husband somehow went behind her back and pulled out a large HELOC.

She'd probably have to get a new loan in that scenario however obviously in order to get you off the current loan unless the loan is assumable, but that's the downside of linking your finances on a 30 year contract without being married. 

If you have lived in the property for two out of the previous five years you could qualify for the 121 exclusion, where you get the first $250k ($500k if married) of the gain tax free.