I'm with you on taking on too much debt, and it being under the LLC name. But I don't think being frustrated with your equipment is a requirement for getting into a hobby or business. I think that's why so many new guys show up here. We don't want to be frustrated. We want to start out with something that fits our budget but that won't make us pull our hair out. It might not always work out, but it isn't necessary.
The first time I pressure-washed a house, I rented a 110v 1.5gpm unit from a big box store. Of course, I didn't know what I was doing. After 4 hours, I was frustrated and told my wife I had no desire to get into the business because it took too long and was frustrating. I've got plenty more stories like that in woodworking.
That day wasn't a rite of passage, it was an ignorant decision. Had I spent time researching, I would have spent $20 more, finished the job in less than half the time, and probably enjoyed it.
I guess my point is, if I'm going to get into a business, I want to give it every chance to succeed. That includes giving myself the best shot at enjoying it. Sometimes that requires decent equipment, sometimes it doesn't. My Festool tools are incredible, but I didn't start out with them and I didn't mind. My Dewalt RO did just fine.
If I'm getting into fences, I'm not brushing stain onto an 800 square foot fence. I may not be able to afford a GX160 powered spray unit, but I'll drop coin on a decent 12v sprayer.