Well ...to start if you are uncomfortable with ladders and siding, rent some scaffolding for when you get to when you don't feel so good...The first 10 feet or so is easy on ladders.
After that any falls will definitely send you to the hospital.
Scaffolding must be the good stuff. Tell the renter what you are doing and they should be able to set you up.
This is much cheaper than say...your deductible for the hospital visit, your time away from work, and if you live....you will be renting it to finish the job anyway....
I hate being .....The safety police....bl-ea
Good luck and don't forget to prime ALL cuts, doesn't really matter with what.