How many times have we said a person interested in doing this should get trained on the job?
2 years in a full service shop can be quite a bit of training for the right person.
I agree with a lot of what is being said about being careful what to buy, saving cash, requiring yourself to being profitable.
The thing I really try to stress to people - designers especially is: are you really good at it? Don't ask friends and family... of you'll end up on American Idol getting laughed at because they all said you are great. Digital print is not that hard once you got the hang of it... in time you might be too busy to design. Is that what you want?
Being in California, you really can't do much more than promotional stuff or
sign fab and install under 500 bucks or you would need a contractors license. You are kinda close to having enough experience to get a contractors license if you are managing jobs. Maybe you can't afford the tools, but a contractors license - or at least qualifying for one - is a good strategic move. I just design
signs, wayfinding systems and branding. Maybe you can be a hybrid of design and some print/install services.
You have some stiff competition where you are at. Maybe not in town, but close enough where getting your foot in the door might make it harder to get clients that could keep you busy to make a decent go of it. Study your competition well. Prepare your marketing to go after company with larger fleets. Get a list of local installers in case you have too much work.