It took me a few years to finally decide that concealed carry was right for me before I did it. It helped that the law as written first in '04 was horrible and got a little better with each re-write and update.
But if you have decided that you will carry concealed, start the process NOW! Don't pick a carry gun now, get the ball rolling on the process. Training, applications, paperwork, wait time, background check, licensing, out of state nonresident permits, all of this takes time. Planning to carry "in a few years" but picking out a carry gun now is, IMO, nuts.
And picking a caliber because of it's historical value? Are you even being serious here? Really. First of all, how is it that 9mm Mak is more historically significant than 9mm Parabellum (1902)? .45 (1905)? Both of these served in two world wars and many other significant wars and conflicts.
In fact, you could pick from a dozen calibers that have historical significance. But that makes about as much sense as picking a carry gun based on the number of times the letter "S" appears in their name.