Great fun pistols, powerful, accurate, simple, customisable (see warning), last forever

I've owned a Crosman 1322 (Medalist) for many years when it was imported to the UK within the UK limits, but these can float close to 6ftlb limit so despite being re-released in 2012 in the US, few of the new 1322's are on sale in the UK.

The 1377 is a different story, widely available. I recently bought one of the newer "black" versions and it's build quality was noticeably poorer than the older pistols.
On taking it apart it has a "bleed valve" to limit the FPS to below 500 for the Canadian market. You'll see on the packaging : 600FPS on older models and 495FPS on the newer
If you're plinking this isn't an issue, it's just disappointing if you're used to the older versions.

To answer the question, yes (IMO) older is better.

Watch the power mods, as the 6ftlb limit is an absolute, so the 1377 platform gives you more "headroom".
Mod a 1322 and you can easily go over 6ftlb, which is about 435FPS with an average .22 pellet.

2240 is a C02 powered PISTOL, 2250 a C02 powered RIFLE, both are great but they are always full power and you have to buy GAS. A pump up can be pumped just enough to get the job done from plinking, target shooting on low/medium power up to small vermin control on full power. A true all round gun that's been around as long as I have ! - Enjoy