|Stretching is definitely a big help, especially as you get older. I've got arthritis in my lower back and both feet and can feel myself getting stiff if I miss out on stretching for a couple of days. I know Brian Wainwright is into yoga and related type stretches.
I didn't say it would take 3 or 4 sessions to get your skills back. I said it would take 3 or 4 to feel "normal" on your skates again. :-) The rubbery legged scared feeling will start to subside. Then every time you skate you'll notice your movements becoming more natural. Within a few weeks it will feel like you were never off the skates. That's the good thing about muscles. Once they learn something they never really forget. They just get a little rusty.
Don't worry about looking like an old fool. When I got back into skating out on the streets 7 or so years ago I used to get razzed all the time by teenagers. I got called "old school" and "disco duck". Now the kids want to know where they can get skates like mine. They mistakenly call them "blades" but that's what they grew up hearing.
Stick with a steady job or follow your passion. I think we all go through that question. I was well into my forties when I figured out how much I like skating. I'm content just to roll up and down the ramp. My body is too banged and bruised to contemplate learning how to do airs and flips. Plus I have an autistic teenage son to deal with so I can't afford to be in a cast recovering from a broken ankle or whatever. If you can have a rewarding job and also do what you like doing best you're doing really well. If you have good sales and promotional skills and can combine them with your passion for skating to get something going on the side, even better. As much as extreme sport type athletes don't like to see a lot of commercialism in their sport it takes promotion to get it and keep it in the public eye otherwise it just fades off into obscurity.