I'd recommend going to a sign expo (I always try to go to the one in Orlando so it's at least a vacation at the same time) and look at the newest equipment and talk to a vendor there. When you start out in this stuff, you don't know how stuff works yet, and you are just guessing sometimes as to if it's you, or the equipment that's giving you headaches. I worked with Advantage Sign Supply right out of the gate 10 years ago, and the previous owners worked with them 10 years before that. They've always been there every step of the way when we had questions or issues. Sometimes it was me, sometimes it was equipment...but you sure don't need to spend hours a day guessing at stuff just to get a good deal.
A couple years in, I couldn't believe how efficient I was becoming, and how much more I accomplished with less supplies. Those first couple years I was just throwing rolls of vinyl away learning how to master the machines. I can't imagine doing that with sub-par equipment, or without someone there to call and ask questions.
If you have another job and don't have to have reliable stuff, that may not apply...but I sure don't regret doing it right the first time since this is a full time setup for me.