With reference to those who I got aggravated with for telling me maybe I'm not ready for the business, I apologize. I took the rest of yesterday and all of today and completely put my business out of my head. I got too wrapped up in concerns over money and insurance that I lost sight of why I'm here in the first place; to cut grass, because I love doing it. I realize that the guys telling me "doesn't seem like you're ready" are (partially) the ones that I wanted to hear from in the first place. I came here asking for info on insurance and received info that I didn't want to hear, and I got defensive about it. Now that I've took some time, I realize these guys are only giving me advice because they have been there and done that, which is what I was asking for in the first place.
So my sincerest apologies to those guys. I may very well put aside my plans to buy a new trailer and use that money towards insurance for this season and pick up a new trailer later in the season if my profit allows. Definitely going to write out how that mulch job should've been priced, however, and have a businessman-to-businessman talk with my fathers boss and hopefully come to a good meeting point on the remaining work required to pick up one of those walk behinds. While I like the idea of having a hydro, I definitely wouldn't be upset picking up a belt-drive for little to nothing (should make a HUGE difference in my cut times, going from a home owner 22 to a commercial 48.) If I have to deal with the harbor freight trailer for another year, so be it. I'm here to do what I enjoy, not be the most profitable and best looking LCO in the area.
Thanks to the guys who helped me realize this.