This is going to be a question of personal preference. There is no really right or wrong answer to this. It will all depend on where your preferences lie and how much patience you have.
Assuming you have multiple guns in each pistol caliber you own, do you prefer to load for the maximum accuracy in each handgun you have or do you want to have ammunition that works reasonably well in all the guns you have in each chambering?
I tend to load ammo that will work in every handgun I have chambered in a particular cartridge. I like to be able to just grab some ammo and not worry about which gun it fits. I have a couple of guns that are special enough that I load ammo that they like particularly well but even this ammo will work n the other guns I own with the same chambering.
I have an older model 60 S&W chambered for 38 Special that wasn't made to normal specs. Everything is undersize, from the throats, all the way out the barrel.
The throats measure .356. The groove diameter of the barrel is just a shade under .355.
I can run some really small diameter boolits in this revolver without leading.
I just run normal sized boolits in it because I never know which gun I am going to be shooting and that revolver is the only one I have with that situation. It shoots well enough with .358 boolits that I can't tell the difference on the target. Perhaps a better shot could tell, but I am not a better shot.
I also have a pre model 14, K frame Target Masterpiece that has every spec perfect. All the throats are .358 and the groove diameter is .357. Wonderful old gun. It likes everything that is .357 and larger.
I still size everything to .358 and go from there because they work in my revolvers.
Since I have so many different 38 Special revolvers, I NEVER push the envelope on pressure in them. I have 357 magnum revolvers for that.
I have 8 different 9mm handguns in everything from a revolver to a pair of 1911s to a Taurus PT92 and a couple of plastic fantastics.
The groove diameters run from .357 to .354 depending on which gun you are talking about. The tightest chamber will accept a .357 sized boolit(barely).
The boolit designs I use allow me to use the .357 in all the chambers without jamming into the rifling. Either truncated cone or stepped round nose boolits.
The accuracy varies a lot as you might expect, but the ammo functions in all of them.
The Taurus guns have Beretta M9 barrels in them. Those are the large groove diameter barrels and the chambers will feed boolits up to .360 without issue. I use .357 in those also but I expect I am bumping those up when they are fired. They are surprisingly accurate with this setup.
The Springfield Range Officer has a tight chamber and bore. I need to make sure everything is right. No sloppy reloads here.
It will still shoot the ammunition for the other pistols but I get an occasional jam when things aren't quite right.
Then there is the S&W 929 revolver. There are no throats to worry about since the chamber doesn't headspace on the case mouth. It tapers from the front of the cartridge right out the cylinder. It will accept nearly anything you can stuff into a 9mm case and doesn't care what the OAL is since there is no rifling to run into inside the cylinder.
My mistake came when I purchased the Taurus pistols first and loaded a bunch of ammo for their generous chambers in those Beretta barrels. I got sloppy because they just didn't care. Now I have a bunch of ammo I can only shoot in those pistols. I have to keep that stuff separate from all the rest and only use it in those guns or the 929.
All the ammo I load now will work in any of the 9mm guns I have.
My 45ACP pistols all have the same groove diameters but have different chamber dimensions. A couple have match chambers.
Everything I load is made for the match chambers and it will run in any of the others. Fortunately, none of my pistols care about nose shape and will feed everything I have run through them. I used to have a couple of 45ACP pistols that would not feed certain boolit shapes due to a design flaw. They went down the road.
I only have one 40S&W pistol so I don't have to worry about different dimensions there. I don't really shoot it much anyway.
Experience has been an interesting teacher.