Conway does seem to be a very engaging candidate in the small number of things I have read. With the reputation he has from his current work, his personality (from the few things I've read) and the fact that he is better looking than Scott Brown, without the vanity would have likely made him a very strong candidate anywhere. The fact that he is competitive in this year (which is hard almost everywhere) in Kentucky suggests that even if he loses, he could be back the next time this seat (or McConnell's) is up.
Best wishes to him.
Like you, I think that Democrats changing the tone and showing enthusiasm - even if not completely felt at first and mocked (as it will be) by the media - could make the enthusiasm real. Remember that Limbaugh himself spoke of how devastating for generations letting the Democrats pass healthcare reform would be. That was likely never completely true, but it was true in the near term. Their own vague plan lists things that it will do - that are actually in the bill - and which they fought. We need to get the good points out. I remember reading that smiling or laughing, even if you intentionally laugh for no cause, physiologically will make you feel more relaxed and happier. Showing enthusiasm is contagious as well and it will annoy the Republicans (reason enough to do so!)
Not to mention, if Democrats begin to look happy, enthused, and more optimistic it could be disconcerting to Republicans and given that enthusiasm is based on red hot anger, they could spin downward if they see the promised Republican wave receding too fast. I have been watching Real Clear Politics, though it is a red site.
http://www.realclearpolitics.com/ They show the various polls as soon as available and blindly average the most recent ones. When a new poll comes in, if it changes the average, they for some period of times put a color coded arrow going up or down - reflecting the direction of the then winning candidate. For at least the last week, if I tallied the arrows favorable to us and to them - we have had more each and every day. Also, at top, the Senate number of pretty sure Democrats has risen from the high 40s to 50 (where the lowest of our "winners" is winning by 6%). There are 4 toss ups (NV, CO, KY, WV). This is the first time I have seen that at 50 or above. This already means, per their assessment, we are fighting over the size of the majority. This is a big deal - and interesting that it comes in the wake of their "pledge". Note that all these polls still have the high republican enthusiasm modeled in. If CW switched to us almost certain to retain both Houses, that very info could dampen their enthusiasm.
(Note this shows us losing PA, where Sestak has had momentum - there is nothing in their average that considers trends. In addition, they have Feingold as losing - which could happen - or when the Senate ends and Feingold is going from county to county as he always does people will remember why they liked him.