Reason number  45,250 that I need to move to Denver at some point in my life 

If the software is not simplifying your life or making you more accurate, you shouldn't use it.

Not to mention I ditched my iPhone 5S for the Samsung Galaxy Note 4 (battery life = sooooo much better, lasted TWO DAYS without charging) and I don't have iTunes on it (and I probably won't install it either). 

I would rather own a home in Class A area for 20 years over Class C and can probably with high confidence say that you will be in a much better spot later in life with Class A vs.

Being at a similar spot in life, I work and manage a fund and most of my personal investments are now very passive. 

Start with the end in mind and building your investing to serve your life. 

Let my license expire in a difficult time in my life.

@Bob Okenwa I have a good attorney and have seen enough contracts in my life that reading through them and understanding what I am reading has never been an issue.

This involved new windows, tile, refinishing cabinets, adding a bathroom, updating a front porch, and several other things to bring this property back to life.

I'm thinking of the expression "whatever works is what works for you" so I'm curious if maybe you should flip this problem upside down and start by thinking things like•What do I want my life to look like in 5-10 years?