Here are my questions- for those professional as well as those who are hobbyists (and professional about that hobby!)
1- What am I looking at besides 4 years of grunt work?
2- Any pro's or cons I need to consider from your perspectives (or retrospectives)?
3- I am looking down the road- not just at my current position- I want to have a shop of my own- How should I approach this (Mentorship, work part-time for another guy, just do it out on my own?)
4- HOW do I start prepping for tool and die?
Your main question is really ''HOW do I start prepping for tool and die?'' I'll show you one path below.
Whether you go to school, serve an apprenticeship, or go it alone really depends on how you learn. If you are a quick study, and have the natural knack for metal working going it alone and hanging out your shingle is the way I did it. I'm lucky in that I ''knew'' how to operate machine tools before I ever touched one, why that is I have no idea, something I was born with. The only hands on experience was one lathe project and one shaper project in high school metal shop.
Let's go back to 1971......
My background was electronics and automotive, and I was working on an R&D project. I took a drawing out to the local machine shop and had some parts built, when I got the bill I was a bit shocked, and figured I could do that. So I ordered a new 12x36 Craftsman Commercial lathe, then found a used Atlas shaper and an Atlas Bench mill. Then bought a drill press and bench grinder. So I have the basics, and was able to play with my R&D project. At the time I was employed as a millwright at a local manufacturer, and they needed machine work done sometimes. I billed them at about half the local shop rates. They had one item that was a high wear part, and I made about one of those a week for them. Note that I didn't quit my day job while getting started. That paid enough that after about a year I was able to buy a new Bridgeport clone and a new 14x40 lathe, and allowed me to quit the day job.
I went out and developed more customer contacts and starting taking in more work. ''Yeah, I can do that''
The most important thing is to have confidence in yourself, and having a high risk tolerance helps too. I have been known to bid jobs without having any idea how to do it and just make it up as I go along. Nothing like a little pressure to get you motivated, being about half crazy helps too.
Fast forward to about mid 1974......
More work means more machines and not enough hours to get it all done. So now I have 3 BP clones, a 3V Cintimatic NC (paper tape, not CNC) bed mill, and a couple more lathes. I also had 5 guys working for me and more problems than I knew what to do with. Lucky for me a guy came along and wanted to buy my shop....That giant sucking sound was me running out the door with his check in my pocket. I took 18 months off, bought an airplane, went SCUBA diving, and built a completely unsafe and insanely fast (200 mph+) '69 Firebird.
Never take on employees, IMHO. A one man shop is the only way to go. Only take on what you can handle. Take care of your customers, but don't be afraid to turn down a job and don't under bid.
About 1976.......
A couple of friends of mine started up an automotive speed shop and they needed someone to setup and run their machine shop, I have no auto machine shop experience but I can build an engine, so yeah I can do that. I also brought in some of my old industrial customers so we did both industrial and automotive. I was there a couple years, then went to work for one of my industrial customers as a millwright again. It was a union shop and they went on strike about a year after I started. Not one to sit around, it was time for another job.
Tool & Die
All of the above experience prepared me for tool & die work.
So about 1979.........
I found a help wanted ad for Tool & Die maker at a local manufacturer. No tool & die experience, but again a lot of self confidence and a good line of BS gets me in the door. It turns out that stamping and forming tool & die work is not magic, it's basic machine work, sometimes to a high degree of precision. But with a surface grinder it's pretty easy to be very accurate. It also requires the ability to understand how metal reacts when being punched and formed. Being able to engineer on the fly is mandatory. Cavity mold work, on the other hand, is magic IMHO.
About 2 years into that job, I'm running the shop and have 7 guys working for me. I stayed there for 7 years.
I spent the next 20 years living on airplanes as a field service tech working on wood products machinery all over the world and writing industrial software to automate systems. Somewhere in all of that I bought more machine tools and have been equipping my shop ever since.
Today I'm supposed to be retired, but my pesky customers won't let me. My primary focus is design/build custom automated machines, with the occasional production job sprinkled in. I still do some tool & die work for a couple of customers. In fact I have a broken part of a forming die sitting on my desk in front of me, I'm trying to figure out how to build a new one. It needs to be in my customer's hands Monday morning.....It'll be there. Because I live in a rural farming area, I also do some farm equipment repair. One of these days if I ever get time I'm gonna get back to that R&D project that started all of this, it still isn't done!
If you are passionate about machine work, love solving problems, have the ability to learn on your own, don't discourage easily, and can project confidence, then you can do it on your own. Working for another shop part time might be a good idea, but don't get into production work. You don't learn much making 1000 of the same part, especially if someone else is doing the setups. A repair type shop is the best environment to learn in, the problem with that is that I'm not sure there are many left. You never know what is coming in the door. Trying to figure out how to best fix that broken or worn widget is always a challenge.
One thing to remember in machine work: As long as shop safety is observed, anything goes, there is no right way to get the job done as long as it gets done and the end result is satisfactory. You have to be able to hang on to the work, reach it with the tool bit, and be able to measure the result. That's really all there is to it.
Best of luck to you.