Regarding the timing… yes, I did look for a painter who could start basically as soon as I was clear of the old siding. That said, we lucked out regarding the weather that summer – dry (but HOT!). There was only a week or two of down time between my finishing the removal of the old siding and the start of hole patching. I used part of that time to repair some of the “ears” which had been chopped off the window sills to install the vinyl.
Regarding replacement of clapboards… some painters can do this, some can’t. And, of course, some just SAY they can… But I had a couple of carpenters siding the new addition, so I asked them to replace a couple of the clapboards that had completely split on the old section of the house, before the painters started. That kind of damage, though, was fairly minimal thankfully.
The only tools I used were a hammer, a “wonder” bar (flat, wide wrecking bar), and a nail-pull. It’s a satisfying task, because it goes fairly fast. Doing it by myself, it took about 5 or 6 days – including loading the dumpster. (oh… other tools… heavy duty work gloves, dust mask, long-sleeve work shirt & long work pants, boots with as nail-proof soles as I could find, and, of course, a case of wasp & hornet spray).