Some thoughts:
Don't put jets just because it sounds cool. That being said, if it's something you want, go for it. I know there's a few other very recent threads that weren't just name calling that listed the pros and cons of the jet and non-jet communities. No doubt you've read them, and I'll let the pointy-nosed homos chime in about jets (I had to get one dig in).
There seems to be a bunch of E-2 guys here now, so they can obviously chime in. I always thought C-2s would be awesome (tailhooker, you're the super hero because you've got parts/mail/cheerleaders). It's just there's no gurantee that you get C-2s. Driving around in circles with the radar going all the time isn't the greatest of fun for me. Of course, that's what I end up doing a lot of in HSL.
As for flying with a crew...I totally agree. When I was selecting, I really liked the idea of at least having another pilot with me, if for no other reason than to pass the time. Having someone in the back is great too. There really is a sense of team and comraderie when you're a crew over a period of time. I notice that most of the pilots and AWs from my last cruise are all still wearing our det patches. Usually you see people get bored and switch them up. Maybe that's just me.
As for the HSL/HSM thing...The transition will probably do nothing but help HSL. There are more exceptions now, but overall, fifth fleet still doesn't really know what to do with HSL. HS guys, bear with me here, but with the exception of the CSAR mission, we do everything HS does, and more, especially with the addition of our radar. So merging the two won't be too big a deal, mission-wise, for HSL, and will probably be a huge boost. Plus getting into the airwing can't hurt.
Now, to add to what I mentioned before...Flying around in circles w/ the radar on can be boring. Every community has got their share of turning fuel into noise. What I love about helos is that on the same mission you're doing that, you also will be down at 50-100 feet hovering/zooming/or generally screwing around. Plus, it's a pretty freakin' good feeling to know that you've pulled some people out of the water that probably weren't going to make it. All of which you don't get w/ the E-2s. Again, not that they aren't an incredibly important asset, because they are.
It's all what you want and prefer. We can only give you some info, but do what feels right. Hope that helped.