Disregarding the fact you should just get experience and work up to it slowly.... (i cannot stress enough how much experience outweighs the NPTC tickets. They really are a bare minimum.) here are my suggestions for your questions:
CS 40 and 41 are not really necessary, reductions and felling techniques should come with experience and 39 really. 32 is not required either, 31 is enough.
I would drop the brush cutter for a blower. the stihl KM tool is good, can be a long handle hedge trimmer, pole saw, etc etc. You don't really need a strimmer or brush cutter unless you want to undertake grounds maintenance work. Blower is essential though.
You might be better off starting with just a transit, stacking and cutting stuff in there, maybe get a trailer too. A chipper is a massive investment, a big risk if you aren't sure that you are going to be a successful business in the next 5 years or so (or even like the job).
Regarding groundsmen, you hire them in as and when. If you get a regular one, you are supposed to employ them on the books really, but you can usually get around it and just subcontract the same person regularly. Don't bother with agencies, just ask around and put an add in a paper or even on this forum. There is no way you can undertake any sort of serious aerial work without a groundsman (or two!) Either way, you will need employers liability (in addition to the public liability insurance that is recommended)
Re lifting big timber? Cut it up smaller. If you want to move big stuff, get an arb trolley or hire a HIAB lorry. Personally i don't see the massive advantage of those tiny loaders, they aren't big enough for timber that is worth milling. I guess its down to what kind of jobs you are getting.
Re stump grinding? If you cant dig it up, recommend someone else to do it until you can afford to buy your own. Its not necessary from the start, and plenty of people can do it after you are done.
I would say start small, see what kind of work you get most. If you get more hedge work, get some nice ladders and a long pole trimmer.
If you get big dismantles, you will need additional big saws, heavy rigging equipment and provisions for moving lots of timber.
if you get loads of small fruit tree pruning jobs, just get a pickup truck, a trailer and a small saw. Hop up with a silky and earn yourself some money to get gear for the bigger stuff.
Spending all that money on training (you're looking at 5k+ for your list), the vehicle, a chipper, the saws, the climbing kit.... There is no way that can really work, you would go bust in the first year, have to sell all the gear, and be at a massive loss. As i said before, and everyone is saying, you need experience first.
Tree surgery is almost like the board game othello. "A minute to learn, a lifetime to master, and hopefully you wont lose any limbs playing"