I would suggest basing your trip in the Dix Range Area for a couple of reasons.
First off, the ski in from Elk Lodge (clear pond) is both long and relatively flat.
Dix range offers the ability to make a fire, thus giving you the ability to dry out clothing.
Dix range is less-oft visited, so if you are seeking some seclusion this is a better bet then say, Marcy Dam.
Lastly, 5 peaks in a relatively small area. Do you like to bushwhack a bit? Slide climbs?
Possible Itinerary:
Day1: Ski In to Slide Brook Leanto.
Day2: Macomb +South/East Dix, return over Macomb Ski the slide?
Day3: Rest, Eat, Be Merry. ski elk lake? possibly move camp to Dix pond.
Day4: Dix/Hough, possibly Ski the slides on Dix.
Day5: Ski Out
Other Options: Do you have two cars? Spot a car at Upper Works, and ski from the Loj over to UW passing through Avalanche pass. Leantos abound in the area and you should not need a tent. (A tarp may be handy) Hit peaks Phelps->Marshall on the way.
Enjoy!
If I had five days, I'd be heading up to Baxter, just my $.02.
-percious