Hi MattinCA,
I've cut and drilled holes every day of my work life. Below are some observations:
Diamond hole saws aren't a good choice for plaster, drywall & similar materials that powder finely. Nor are they suitable for soft materials such as gypsum based anything. The dust clogs the spaces between the diamond grit dust, stopping them from cutting. They're more suitable for concrete, granite & similar hard materials.
Klein gave me Klein 53710 adjustable to evaluate. It's OK, but S L O W (as are all of that type).
It can also rip the drywall paper if you're not careful. at the start & end of cuts.
But, I cut an awful lot of holes with it and it's still cutting well. It never lost it's adjustment- not even once. (Others I've tried do. It can wreck a hole quickly!)
I prefer traditional hole saws with arbors. Push-pull arbors, such as Starrett's are convenient. You can get bi-metal (usually M2), carbide, diamond. The bi-metal are easy to sharpen when needed. I recently used a 5-1/2" Starrett Fast Cut for many holes in plaster-on-metal, wood & blueboard laths. It held up well.
If this is a one-time-use tool, maybe try a cheapie one from Temu or Harbor Freight. When you're done, drop it in the recycling bin.
*HINT: Be Sure you know what is above where you're drilling. Wires? Pipes? Ducts? Structural? The cat?
Enjoy Your Project!
Paul
You Didn't Ask, but here's an unsolicited editorial about your wiring plan:
Since the equipment grounding conductor in the new NM cable is not grounded at the source, you're supposed to snip it off flush with the jacket in each box so no one thinks it is usable & attaches it.
To leave it disconnected from earth creates what's called a "Floating Ground". This can be quite dangerous.
(Caveat: Although a master electrician, my career was primarily industrial & high voltage distribution, so the preceding sentence is based on jobs helping friends in houses & rehabbing buildings that I owned.)
Also consider that many LED dimmers won't work properly without a grounding wire. The lamp(s) will clip at about 10% brightness.
This snipping certainly messes up the project when you do have a chance to ground the circuit, so If at all possible it would be a good time to fish this cable back the the load center & ground it.
But All may Not Be Lost...
Test the boxes in your home for grounding. They might be grounded and you don't know it. If your house has BX cable (common in the 20's - 60's), the trace wire might be bonding the box at the clamp where you can't see it.
To Make Re-Wiring Less Intimidating-
As far as re-wiring the house so everything has an equipment grounding conductor, think of the job in a piece-by-piece fashion. How often do you need a 3-prong, grounded receptacle outlet in the living room? The bed room? They can wait- or be skipped.
Also while working on the re-wire, you might as well update to new code rules.