Thanks for the long reply. It makes sense for sure. I'm definitely not the "cheap" guy and I do get plenty of "no thank you's" over price or the fact that I won't cut fescue lower than 3.5 inches.
My truck definitely isn't new "1996 Cummins 12V" but its my third child and I take care of it and all my equipment is pretty new and taken care of. I would say I look better than 85% of the guys riding around doing lawn care. I see tons of guys with a ford ranger or the wifes SUV hauling a trailer and an old beat up walk behind (nothing wrong with that if it gets the job done) and I know they cut for hire since they have "Joes lawn care" plastered all over the vehicle saying $20 lawn service lol.
My goal is of course to make money, provide the highest quality work "perfect stripes, perfect edging, no clippings in beds, etc..." and live comfortably and be able to support my family.
I may need to try raising my prices even by $5 but I may wait until next season since this season has already started.