Thanks for all the replies, guys. I did purchase the ART mymonitor, received it yesterday, and i'm really liking it so far with the minimal time I've been able to spend on it. Luckily I can easily return it if I'm able to find some way to finally get what I wanted within the Scarlett itself, so I'll be using some of these suggestions today and fooling with it one last time.
As to some of the specifics asked, I'm using an AKG C214 mic, along with AKG headphones. Can't remember the model of those phones; they're not top of the line, not terrible either. Decent mid-range pair.
I think my issues comes down to the gain I've been setting on my mic. When I set it initially, I would carefully watch the meters as I sang some test passages, and everything stayed in the green, no yellow/red. But when I would play back. louder passages would have a sort of clipped sound, almost as if someone had applied a way too-heavy brick wall compression on it. I had a pad that came with the mic switched on while singing.
Anyway, I found I could remedy this by lowering the gain volume to the point where the green level indicator on the Scarlett barely comes on while singing these sections. The result is that the vocal doesn't have that "overly compressed" or distorted sound, but the result of THAT has been that the levels in the mix have been too low for me to really hear well, even with everything in Sonar's mix control cranked to full volume for the vocal and lowered as much as possible for the music mix. I tried to remedy that by applying input echo, getting the latency low and adding some compressor to the back end in Sonar while singing, and that's helped, but has also brought some other issues into the mix (pardon the pun), i.e., not totally comfortable now with the processed sound of the vocal coming through. I know, nitpickery.
I think a lot of it comes from how I sing certain parts - very loud, very hard, and my songs tend to usually have some pretty big changes in dynamics. I've already done separate tracks for a "softer" verse and a "harder" chorus, so I'm not singing both of these parts on the same track during the same take.
So yeah, maybe there's a technique thing involved that I need to work on, but I do know enough as far as when to back off the mic, get up on the mic, etc. In any case, thank you for all the great replies. I will have some time this afternoon to fool with this some more, but hopefully the above explains my situation a little more clearly.