How many times can you reload them before they start to loose accuracy ?
Do you guys keep track of how many times you reload them and keep the separate as in groups of once fired, twice fired etc, ?

I don't think you will notice a degradation in accuracy. Usually the necks will split or the primer pockets will get loose, but I never noticed accuracy diminish due to multiple loadings. Keeping a group of cases together and tracking the number of reloads is a good idea if it works out for you. Usually, I wind up shooting a number of rounds out of a batch and the cases wind up mixed up with others from another batch.

Actually the 2nd or 3rd reload is probably the most accurate. Then other issues begin to crop up that annealing can fix. I load five times then recycle. .223 brass is too common and cheap to expect much more than that from a semi-auto.

I can't honestly answer the first question not for .223 in a semi auto anyway.

As for the second part there are a couple ways to go about it. When I first started to "collect" .223 brass I was going to prep all of it then work my way through it.
Well the collection kept growing and growing so I decided to separate it into lots. I have different brass for different things so the lot sizes may vary.

My varmint ammo for example is weight matched and it is only 50 rounds. My deer ammo is the same. I'll cycle through these until the necks start to split then scrap them. I won't bother annealing .223 brass. I haven't noticed any accuracy loss with the varmint brass yet but they are only on about the 3rd cycle.

I have not noticed any accuracy degradation and I do not chart how many times my 223/5.56 brass gets used. I do look for signs as mentioned above and toss when I encounter. Ditto on this brass is just too common to be expending effort to anneal and separate.

Vince