45 Auto, 200 SWC is easy, the .40 S&W and is surprisingly easy to load, IF you just go for moderate/easy shooting loads, lots of cheap brass. 45 ACP has advantage of large or small primers if you have/need them. The 9 is NOT a reloader's friend, high pressure, small case volume, case taper make for more difficult reloading. .380's not bad, .32 ACP about the same as .380, milder pressures but they are small to handle. A S&W 52 in 38 Special shooting full wadcutters may be the 'best' cast bullet fun pistol.