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Imho, semi first then the wheel gun.
I started with my Sig 1911-22 to get a feel for the 1911 chassis and plink for cheap. Then moved on to the IWI 9mm in steel. It's a beautiful shooter. Next will be a 357/38 special revolver. Something about the mechanical nature of a revolver just makes me smile.
That said, you can't go wrong with a Glock. They're popular for a reason, and I find they fit well in your hand. As for the larger caliber, the 44 was chosen by the FBI to replace their standard 9mm when body armor became more common. They couldn't take down a perp without multiple shots unless they were using the large caliber. So unless you're a wealthy mofo who can afford to blow off $5 every time you empty a mag, or you need the stopping power, it's not worth it to go the large bore pistols.
I had a lot more fun shooting a 38 special at DVC, than the 44 magnum my brother was shooting. Don't get me wrong, I'm no pussy. I'll shoot my Remington 870 with 3" slugs from my hip without breaking a sweat. But that 44 mag was a cannon, for sure. Honestly, if you're going to go big, go Desert Eagle big with the 44 mag/50 cal kit with interchangeable barrels.
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