Here's another idea, going in a different route altogether. You are going to use sent back, so just plan on Gandalf dying every turn or two. Don't worry about healing him. Run plenty copies of his sword and maybe wizard's staff and reload him each time. Or perhaps use These are My People to get his toys back before moving on.
If you go this route, you could
Saved From the Fire Gandalf when he's about to die to get another Gandalf and two of his items. That way, you can play him immediately and don't have to take on a site without him. You could also use
Fireworks to recycle Gandalf's gear back into your draw deck for
SFtF, and
Barliman Butterbur, PPP, to get
SFtF or
Fireworks when you need it. Of course, you'll be adding a lot of twilight each time you do this (
The Nine Walkers helps a bit with that). I even have a name for this strategy: Phoenix Gandalf.
Alternatively, you could use
Gandalf's Cart to store extra copies of his stuff.
EDIT:
Gandalf's Wisdom could also help with the twilight.