Yea, handcrafted does mean finite replay value, whereas AIW's is arguably getting into the functionally-infinite (in that you can get tired of it but not probably not because you ran out of genuinely new scenarios), but it doesn't mean a low replay value. There's also the angle of community content and (possibly, not sure where Chris is on this) ongoing stuff from us depending on how well it does financially, etc.
Yes, while there will be finite replay value, we hope to have enough levels in there to still make it a fun experience worth what you paid for it. There are already close to 100 levels in it right now, and we'll be adding more as development continues, in fact, I'm working on another right now.
As for community content, there's definitely room for that on this one. The level editor is actually really good, quite polished right now. We plan to add good levels from the community into the game similar to how we add rooms to AVWW now.
LaughingThesaurus is right, there's not really a way to have procedurally generated levels that make sense and are also good/interesting, so they have to be hand-crafted, but, IMO, a hand-crafted level that is done right can have a certain amount of character that a computer just can't generate.