I work in the home energy field, and used to work for one of the big players in that industry in the Bay Area. Based on your decision not to DIY, I would seriously recommend that you use a general contractor to coordinate this work, rather than hiring an electrician, roofer, insulator, and handyman and trying to manage it yourself. Unless you have experience in construction, all these different trades will end up working against each other and screwing up each other's work if there's not a GC there to coordinate it all.
As far as workflow, you should plan to do things in this order:
1. framing (dry rot) - can't wire, plumb, or insulate if there's nothing to run it in
2. skylights - placement may affect electrical and doing skylights after roof is begging for leaks
3. electrical/plumbing - you may be running wires around the skylight wells and/or pipes and wires may penetrate the roof.
4. roof - if you do the roof after you insulate the ceiling, the roofers are guaranteed to screw up the insulation, especially if yo do a full tear-off.
5. insulation - if you do this early on, the framer/roofer/electrician/plumber will ruin it
6. finish work - they call it "finish work" for a reason.
For wall insulation, you are most likely going to want to do drill and fill cellulose, which will allow you to get insulation in the walls without having to gut the walls.
For the best results as far as comfort/environmental, you're going to want a GC that specializes in energy efficiency (also called building performance or building science). If you want a couple of recommendations, I will be happy to accommodate via PM