I'm a fan of "what if?" type questions so I'll play along. It's always fun to not only reconsider my past choices but to see other people's responses as well.
When starting off with my original purchases, I was faced with a couple of limitations. First I was a right-hander who prefers to shoot left because of a bad right eye. So as an involuntary southpaw, I like ambidextrous single shots. They work really well for a lot of the hunting I do so I acquired four Ruger No. 1's and four 1885's. I was stuck in that enjoyable purchasing groove for a while.
Another thing that narrowed my choices was left-handed bolt actions come in a smaller selection of chamberings. Some desirable classics like the 257 Roberts, 7x57, 300 H&H and 35 Whelen (Ruger just announced one!) were never made in factory left-handed rifles. Left-handed DG rifles can be harder to find as well. Fortunately, I really like one of readily available options in the boringly dependable 30-06 Springfield which is why I own three. Setting up each one for a light, medium & heavy bullet, I can cover a lot of situations with this one cartridge alone.
But to answer the OP's original question, if I had to start over, the majority of my small collection would stay. I've never sold a rifle & I really like everything I have. One change I would probably make is I would have gotten a nice kipplauf rifle (
e.g. Blaser K95,
Merkel K5, Kriehoff Huberus) in a rimmed cartridge like the 7x57r or 7x65r with a neutral butt stock. Maybe add an additional barrel in a smaller rimmed cartridge like the 22 Hornet.
I'm not much of a shotgun guy but I would like to own a cast-on SxS for upland hunting like the
Fabarms Autumn in 20ga. I do my waterfowl hunting with an ambidextrous Browning BPS 12ga but might consider upgrading to a left-handed semi-auto if I go goose hunting again.
My current rifle safe looks something like this:
DG Rifle: Winchester 70 Safari Express (LH) in 375 H&H, Ruger 77 MkII (LH) in 458 Win Mag
The workhorses: Remington 700 (with a Timney trigger), Sako 85M Hunter & Steyr CL II all in left-handed 30-06.
The 3 Amigos: Ruger No. 1A in 6.5x55, Ruger No. 1 RSI in 275 Rigby, Ruger No. 1A in 303 British. Each one is as good as the other for the deer hunting I do in the southeastern woods & I love them all. The Swede shooting 140gr Partitions has put the more deer in the freezer than any other rifle I own.
Straight Walls: Winchester 1885 Traditional Hunter in 405 Win & a Browning 1885 in 44 Magnum. My early primitive season choices for Arkansas, Louisiana & Mississippi.
Hog Rifle: Wilson Combat Protector Carbine in 300 HAM'R. Semi-auto speed with 30-30 power using 130gr Speer Hot-Cor's.
Varmint: Left-handed Cooper Model 22 in 22-250 Remington and a Browning T-Bolt (LH) in 17 HMR with a varmint barrel.
Small Game: I do most of my squirrel & rabbit hunting with a Weihrauch HW77 pneumatic. But my Browning T-Bolt (LH) Sporter in 22LR is very accurate as well.
My personal favorite stalking rifle: Ruger No. 1S in 9.3x74r with a Minox ZA-5 1.5-8x32 scope.