You'll find the roads a lot better than 15 years ago until you get to West Clare, (west of Ennis.) After that they're much the same. Going to Ennis via Kilaloe is the scenic route - if you've got the time it is a lovely part of the country. If you're in a hurry head for Limerick and take the main Ennis Road - many of the heavy traffic blackspots on this route have now been bypassed, but I'm not sure about the current state of roadworks in the area. Matt the Threshers pub in Birdhill is a good place to stop for a meal - at least it was until a couple of years ago - I haven't been there lately.

Geoff Wallis' recommendations for sessions in Dublin are good ones. If you like unaccompanied singing the Góilín singers club meets in the Teacher's Club in Parnell Square in the City Centre on Friday nights. The 4th is probably their last meeting before the summer break and is usually (I think) a good night, but I'm not a regular attender. As well to check before you go - I think there's a website.
You'll find a lot of the people you meet there will also be heading to Miltown on Saturday.