BTW, I've never heard of a "model 300 model 99".
It's a 300 Savage chambering.
I agree...
If that is what the GS said, get the gun to a good gunsmith, yours should not be messing with firearms!
The rear of the bolt 'locking' area (both bolt and receiver) are subject to wear, and is often found, but it takes a bunch of shooting!
Another headspace issue cause is on take down model 99's. Assembly and disassembly (a whole bunch of it) can cause wear on the interrupted thread arrangement (the take down feature) on both the barrel and receiver. When that is the cause, it is usually pretty apparent as the barrel will show varying degrees of 'wobble' when handling the rifle, mostly with forearm removed.
In my opinion, it would take a bunch of excess headspace to cause the firing pin to only on
occasion fail to strike the primer. If it were a headspace issue, it should happen with more regularity.
I think you have a different problem. Most 99's are getting pretty far along in the years, with many not having had the best of regular maintenance. It may be a simple case of 'gunk' inside the action and/or bolt interior that is causing sluggish firing pin fall, give it a good, thorough cleaning first!
See it you can put a couple of thicknesses of paper (each about .003" - .004" thick) between the back of the bolt and the receiver and see if the lever will completely close the bolt....That will tell you a little a bout the headspace.
As has so many times been said on this and other forums, photos tell us a bunch when it comes to trying to assess a problem and provide answers and assistance. Take close photos of the bolt lock up and of the primers of both fired and failed to fire cartridge cases.