I don't know the boat personally but here is the general spec for it:
EASTWARD HO 24 sailboat specifications and details on sailboatdata.com
Seems like a boat with a pedigree.
Also interesting is that my Tartan 27' only weighs 7200# and your Eastward Ho is rated at 7600#. Seems to have been designed and built for longer passages.
Extrapolation: a boat like that (similar to mine) will not be a great light air sailor but should be able to put up with some rough conditions if you can.
As for maintenance issues I'd assume the usual suspects: chain plates, mast step, soft decks, yada yada.