Wesson has two quests, a Orobas Fjords quest, and a Flying Fortress quest, each gives you one upgrade, and as far as I can tell, Radcliff only has one quest, an Orobas Fjords quest that gives you two upgrades if you return the gem to Radcliff, and one if you trade the gem
to the 2 goblins that approach for 2 malachite gems. If you outright refuse to trade, then you'll be thrown into a boss fight with 2 dangerous flying Goblins
.
Malachite gems are really nice, but I pretty much NEVER use them, because there is a finite supply, even if that supply is over 40 (counting FoV), and the Rank 9 enchantments are infinitely reusable, and are pretty good.
Also, if you have Radcliff and Wesson compete, then pick Radcliff, the cutscene
shows Wesson ans his wife Ginny sobbing uncontrollably, before the bolt from the blue kills Wesson right in front of his wife. Then if you talk to Ginny she calls you a horrible monster and hopes everyone YOU care about dies as well.
That was pretty my entire motivation for picking Radcliff on my evil character.