I would keep the .30-30 and then buy a T3 as you mentioned, top it with a very good scope. Spend the rest of hunting, shooting, ammo, components, range memberships etc.
Chambering: I would be equally happy with .308, .30-06, .270, 7mm-08 for an an all-rounder. If keeping the .30-30 I like the idea of a .270 win a complement to that.
If getting new rifles to start on a clean slate I like your idea of a 6.5CM and .30-06. I think 2 T3's and 2 decent scopes will push you well above $3k and with Vortex on a hardworking big game rifle I would not use any model below the Viper. I prefer VX-3' to my Viper.
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