The siding removal is a relatively easy process. The labor intensive part will be filling the holes left from the siding and felt paper removal.
Our siding was was put on in the 1920's and that means you should always have it tested for asbestos. Not all siding of this era was asbestos based. Ours was mineral wool based. However since this stuff is old and dusty you should take the same procedures that a contractor would if dealing with it. Wear masks and you should tarp the ground on the worksite (this makes clean up easier). You should also use proper disposal procedures. Also if you hire a contractor to do this kind of work be aware all contractors are now required by law to have a trained and certified lead abatement tech on site everyday to insure that proper containment and disposal procedures are used. This should always be speced out on any contract you have. If its not find another contractor.
When you consider this siding was 57 Year old when it was covered over is testament to prior owners who really cared for and maintained their home. This usually looks much, much worse! You realize how grimy things were back then as this was a light yellow originally!
I have to admit I was surprised that this siding was in as good a shape as it is. Perhaps because we only have two windows on that side there was less opportunity for water to seep in and overall and so far, the siding is in remarkable condition. The siding will need little scraping so the procedure here will be to do any replacement that it needed. Sweep and than hand wash the siding down and then begin the priming and painting process. The drip edge at the bottom will have to be restored (its a board that helps water shed away from the foundation and helps preserve the stone work (also in pretty decent shape although I will have some mortar work to do).
With any paint job the better prep job, the longer you paint job will last. A good paint job can last 10-12 years with good maintenance.