Nails usually lift, especially with time, especially on shittier wood (like OSB). You're entirely depending on someone to hit the nail strip every time and seal every hole that the head doesn't seal on that strip. Most don't give a fuck and I've seen "professionals" leave bare nails below the strip but above the reveal... where there is a seam on the course above.
Next layer of shingles gives you a better chance of hitting another obstruction (like another nail) especially since shingles are usually the same size every time. Switching from 3 tab to metric dimensional can help with that. But again, lazy roofers are more than likely going to leave a hole.
If you don't strip the deck, you will never know if you have any damage.
If you don't strip the deck, all roof penetrations are largely going to depend on sealer. No one is going to bother doing a good job. They're just laying down product and dabbing on minimal sealer.
A bundle of shingles is not free weight. Most roofs are rated for at most 40lb/sqft.
Shingles depend on cooling being provided by the roof vents. If there are two layers of shingles they can't get rid of heat as well. You want everything above your insulation to be ambient temperature year round.
The hard part of roofing are the houses with a lot of roof lines like was popular from the late 80s through the late 90s. The ticky tacky boxes built since usually have the most simple roof lines because they usually are even missing a bunch of penetrations (everything vents through wall except maybe a soil stack or two) and everyone was too cheap to pay for dormers let alone elaborate roof lines with lots of ridges and valleys.
Stripping the roof of shingles should cost you:
$300 per pallet of shingles for disposal. A pallet of shingles is usually 36, 39, or 42 bundles.
The labor to strip the roof. Not rocket science here, one person can do a pallet worth per day with plenty of siesta time.
The materials and labor to put down more felt (synthetic or tar paper). Nailing the synthetic by hand will cost a lot more than stapling tar paper, but the material costs the same.