These are not RAW, erratta, official advice, or anything other than one DMs ad hoc call: In general, I let druids/polymorphers choose what gets subsumed, while I choose what might reasonably stay on and/or provide benefit.
Bag of Holding easy for the eagle to carry, but that prevents other uses for that talon, so it's a trade-off. The bear could carry this in its mouth, but risks puncturing (ruining) it.
Belt of Many Pockets too tight for the bear (and the bear would not be sufficiently dexterous to retrieve anything from the pockets anyway. Eagles don't have waists. Ergo, they may not wear belts.
Hewards Handy Haversack The eagle can wear this if it chooses to forego flying while wearing it . . . no wait, how big is a dire eagle? If it's larger than the PCs normal form, then no, no wearing it, flight or no. The bear might be able to have a fellow PC cinch this item donw on one of its forelimbs, I suppose, but then you's still have the problem of retrieving stuff from inside without spilling all of the contents out onto the deck. Since somebody else would have to resecure the buckle/strap/whatever anyway, The bears better off subsuming the bag or handing it off before transformation. It's possible, but prohibitely inconvenient.
Circlet of Blasting I don't remember what this does off-hand, but if it takes the form of a headband, as I think it does, it's not going to stay on either an eagle's or a bear's head. Even if you rule that the band resizes, these creatures' heads are just the wrong shape for human headgear.
Hat of Disguise The player may argue that this hat should have a neckstrap: that's fine. Personally, I think it should. It changes its appearance to blend in with the disguise. I've always just let PC wear their hats of disguise whenever they want. "Hey! Look at me! I'm a dire eagle that looks just like a dire bear! I'll bet you've never seen a flying dire bear with a salmon balanced on its head before!" The exceptions might be creatures with wonky heads AND no necks - no HoD for dire octopi.
Boots of the Winterlands Boots are normally made to fit feet. I guess you could make some garment to fit paws or talons, and if you wanted to, you could call them boots, but no. the same item will not fit feet and paws and talons. These get subsumed, abandoned, or ruined.
Periapt of Wisdom +6 increasing the
possessor's Wisdom score, not the
wearer's, it could be argued that you don't actually have to wear this to gain the benefit it affords. In this case, have the party's leatherworker come up with a harness for the beardruid to use this with. Otherwise, if you rule that the PC has to wear this item, Id say the eagle could wear it, but risks losing it, while the bear simply can't wear this item.
Grogtar said:
The real question is which (if any) of these items will switch over when he
wild shapes ? His favorite forms are dire bear and dire eagle. We are house
ruling it now that all of it still gives him the bonus’s or abilities when
he wild shapes and it is proving to be overbalanced.
If it gets subsumed, it stops working while it's subsumed, unless you've got that other magical item, the name of which I forget, to prevent that. Only items, held, worn, or otherwise attended (ioun stones) continue to function. Subsumed items do not.
