advice?

[zenda2]

(Putting on kevlar bodyarmor and helmet)

One of the few wine and food matching rules that actually works out for me is drinking pink wines with pink meat. So another option with ham/pinapple could be a pink wine, perhaps even a White Zinfandel if you want a sweeter choice with the pinapple.
When I serve ham I usually drink bone dry pink wines like Tavel or my personal favorite, Bonny Doon's Vin Gris de Cigare.