I'm in the midst of gaining my license, and I'm wondering how those of you who are licensed who also flip handle your buying and selling commissions. 1.

It may not be a fit for your financial goals, but if so it could be a way to gain some experience and insight as you work through a two year timeline.

I remember I was more fearful about house hacking, but as I read more books on real-estate and house hacking itself, I started to gain a better understanding of what I should expect and what I should do.

Should gain a healthy amount of equity in that time with the market and paying down.

@Ross Y. as @Jai Reddy said, with the extra info you provided in the second comment, that your wife qualifies for REPS, you can certainly use the extra losses from cost seg, beyond your rental income, to offset your W2 as well as the other active gains. 

My experience has me doing well on renovation budgets, but I’m having issues with understanding comps in the sense of equity gains from renovations.

Is my Capital Gains 100K?

I’ve read stories about people buying a portfolio but having each individual property appraised prior to purchase, and then either cash out refi or sell individual properties out of the portfolio for substantial gain.  

The bridge is in rough shape and the engineering firm I had looked at it said that it would only support the weight of a pickup truck but would not support the weight of a cement truck or larger weights required for development or required by the fire marshal.

I have also gained tremendously from @Brandon Hall's podcast/youtube channel The Real Estate CPA, as well as their FB group.