Not sure if this should be under psychology or a different forum but here we go.

For the past few years, pre Black Friday til today I have prided/beat myself up over my attention to small ball and good bankroll management. My friends and other have different "tactics" to level up and gain money, our styles clearly differ.
When I would first deposit online (FTP) I usually would deposit the min or somewhere around it(I live 1.5 hours from Foxwoods and Mohegan sun and have a handful of local rooms available if I want to play for significantly more $) I would use online almost as a training tool. When playing live I am usually playing 1/2 or occasionally shot taking 2/5, so as far as mental competence for the game, I feel comparable to the field. Online I would/will play micros and try and grind up a decent win rate but as we know micro players love to call 4bet jams with marginal air at best. So my variance takes a hit in these stakes and as I fight through I will play some 10 to 25nl feeling like these are the levels that have the most "thinking" players.
On the flipside my friends who play live/online do the opposite, will deposit more and immediately be sitting with 50-75% of their roll within minutes. They can have mixed results but i find myself asking, "how do they not just play it safer n run it up?"
I should have prefaced by saying I am recently engaged, have a rent payment, a 19 month old son, so my priorities are a bit different than my friends. My question is, do I add some gamble? Am I playing it TOO safe?

I think you are trying to compare yourself to your friends. If you were happy with your win rate/situation, I don't see any problem. You wouldn't want to chase your friends's results and play over your bankroll and go bust.

Doing what your friends do is wildly reckless. The only way I'd even think about dropping $100+ and playing for half of my bankroll or more is if I knew for an absolute fact that I could beat higher limits, didn't have the immediate bankroll, and was willing to take $100+ shots as I was able until I ran good.

I'd definitely continue taking the time to grind your way up safely. It really is the best format. It gives you alot of experience and builds up your confidence so much. It may seem like a waste at first in the micros, but eventually you will be making significant money backed by more solid experience because of what it would take you to get there.