I'll build this list from what I currently have rather than building my "wish list...." I have lots of wishes.
#1) Ruger 10/22 .22LR with a Nikon prostaff 3-9. just a fun plinker that is able to be used on small game as well. Lately it's been getting a workout as a chicken protector as I've had lots of predators hanging around the coop lately it seems. It's reliable, accurate enough for me, I've been shooting it for 25 years, I have confidence in it.
#2) Mossberg 500 12 gauge Similar to the 10/22, I just have allot of experience with this shotgun. I bought it with lawn mowing money almost 20 years ago. It's ugly, and well worn. It's been beat, but it's been used on everything from clays, to squirrel, pheasant, grouse, woodcock, rabbit, coyote, deer, turkeys, geese and ducks. I've probably owned over 100 shotguns since buying this one, but this one will never leave the safe. Too many miles on it to think about selling it.
#3 Remington 700 .30-06 Leupold VX3...Reliable, plenty of thump for anything I'll likely ever hunt. accurate, lots of easy to find ammo.
#4 .458 WIN CZ550 Safari Mag If the '06 cant handle it, then this can. I was tossing up between this and a .338 WIN MAG... However, I don't see enough of a performance jump between the '06 and the .338 to justify putting it in here. the .458 definitely can handle heavier game.
#5 RugerBlackhawk in .44mag This revolver gets the nod only based on my limited options. I need to have something powerful enough to do the job, even though 95% of the time the .44mag wouldn't be ideal.
This list was made with hunting in mind, if defense and duty gear comes into play I would need to drop the .44mag and the .458 win and add my Glock 17 and an AR15. But since we focused on hunting I left duty gear out of it.
Missing from my list are a small bore rifle, rimfire revolver, lever action rifles (what I really enjoy the most), and some other shotguns. But since we're limited to 5 I feel I could hunt anywhere in the world, for the rest of my life, with the five listed.
-Jake