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. 

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.

(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?

I have seen instances where a 1031 exchange was not required such as1) The overall gain from the sale of the investment property was very small or even negative2) The taxpayer had enough passive loss carryforwards to offset the gain.A 1031 exchange is a very powerful tool put it has to make sense before going forward.

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. 

The tax payers of the world cannot pick up the tab for this waste of energy and so-called "innovation."

If you are married - put each one in a single name and you can then have 20 - there are higher qualifications the more  you have though.

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.