Well, I think most guys here would set the jetski out back to make room to work on their bird. You have a beautiful car; I checked it out on your links. You won't be sorry to bring her up to snuff and storm through town with that car. Your car will certainly turn some heads and you won't regret spending money on restoration. When you get bored, drop her off here; I'll make a good home for a red '69.
I do think you could and should take on some of the mechanicals of the car. Nash suggested that, but he may have put some complicated tasks on your list. Pulling out the engine is a bit much as a new project, but some things on your list are easily paid for with your time and even buying some new tools. Remember that tools last a lifetime and experience is knowledge that enhances life experiences. Patience grows with experience and if this is not a daily driver, you can park the project when your patience wears thin. Just walk away, sip a beer when you get annoyed and come back later. On an old car, you need to know your way around the mechanicals anyway, because the reliability is lesser than a modern car due to the age. These older cars are comparatively simpler. You can and maybe should take on the easier mechanicals and work your way through as your experience builds your confidence. If you can navigate around IP, internet backbone and such, spinning wrenches on rusty bolts won't be a technical limitation for you. The steps of sorting through technical issues are very much the same and the physical issues of pulling on a wrench won't pose problems for you at your young years. Memory leak or oil leak... pretty much the same thought processes. What caused it and what's the remedy? The harder stuff can be explained by folks here.
I started out in '68 changing the points in my bird. That was my first experience that side of the hood. I ended up tweaking them again at the roadside on my way to school because it ran like crap. Don't be afraid to take on stuff outside your experience. You can always do it over. It starts off with minor projects like points, condensor, thermostats or shocks and soon you learn the whole car as you go through it.
A big awakening for me was when in 1969 I asked the Pontiac dealer to replace a worn rubber brake pedal cover. I was astonished to be charged a half hour for that three minute repair. I was 17 at the time, lol. I guess I figured that would be free as a three minute fix. The shop was justified in the charges though. Someone had to go request the part from the window. Someone had to order it in. He had to install it. Someone else had to put it on the invoice. A half hour was reasonable, but it was not money well spent. Everything has cost and profit in it, even for a three minute task.
All of this stuff, I've done once and many times done over again after the first attempt failed. I still have some things to do over again, but I learn as a go through the car. Doing things twice is still cheaper than paying to have it done. The good thing about doing some things yourself is you know whose as$ to kick when it's not right. That makes the going easier. I know I've wasted valuable time over jobs I paid for that were done incorrectly by others and the effort to set it straight many times is more than DIY from the start. Setting blame is always 1/2 the problem; you know from your life experiences at work that until you set blame, nothing gets fixed! Once blame is set, problems can be solved.
You have lots of smart guys to get help from here, and most of this is turning nuts and bolts. Okay, many of them are rusty bolts, but still it's workable. Put the shocks on your own list of repairs and fund the repair with a set of sockets and a wrench handle from Harbor Freight. You will be amazed how much work you can do with a cheap set of six point impact socket from HF and a wrench handle. That $10 set of sockets is nearly my favorite kit, over the craftsman or other sets, because it won't round off bolts and I can beat on them.
You'll be amazed what you can do when you get going. It's so worthwhile too..... The Pontiac dealer cross-threaded a rear shock on my bird back in 1969. They declined responsibilty when I couldn't change the tire using the bumper jack.... and I didn't know they did the job wrong until I couldn't lift the tire off the ground with the jack. It went back to setting blame. Once the dealer declined blame for a lousy repair, it still needed to be fixed. I bought a tap and rethreaded that shock and fixed it myself. There's just a nut at the top of the shock and another nut at the bottom, then it pops out. Give it a try on your car as a good first project. Changing your own shock also gives you the choice of selecting a superior shock vs a generic part.
Some of what I'm thinking is that repairs are $60-$90 per hour. That is sort of a reasonable price these days and weather the repair is complicated or simple, an hour labor is still an hour. When it's work you can't do yourself it's money well spent. Like pulling the engine... not a good first job for DIY, unless you're determined and patient like Nash or myself. When it's changing a shock, you pay yourself well to DIY. The shop can't charge less because the job of chaning a shock is less complicated than pulling the engine out, because it's the same talented mechanic doing the repair, weather it's a shock or an engine repair.
The steering gear job you listed is probably $450 worth of labor, excluding the parts. It's not a hard job, other than popping the pitman arm loose. Three bolts hold the gear to the frame. Two bolts tie the steering shaft to the input shaft. One nut holds the pitman arm on the output shaft. Two lines connect the hydraulic lines for power steering. At worst, you would spend an entire day. If you did this a few times it's two hours work or less on a bird. You can do that yourself with $100 or less worth of Harbor Freight tools and an afternoon. You'll finish with confidence that all the bolts are tight too. Okay, it's a [censored] to pull the pitman arm loose sometimes, but we'll all help you here or at least offer our sympathy. You will come back telling how it was a [censored] and then it fell loose. And I never heard of one that couldn't eventually come off with a large hammer.
You have a couple of items on your list you could take on yourself. They would be learning experiences that give you great confidence in owning and driving this car. Tools will be cheap and last a lifetime.
On the other hand, there's nothing wrong with dropping the car off and having it done for you. In that instance, I think the prices you've been told are fair and reasonable for this much work. The mechanics and shops have a fair profit just as you have in your profession. I don't think you're being taken advantage of with what you are quoted. It comes down to the best use of your time and chance to advance your understanding of mechanicals of the car.
