Underworld still exists, but as to which town I'm not too clear about. I just remember there's a portal that gets you to the underworld and it wasn't really in a town.
About your PvE questions, I'm going to pass and not give you my guesses because I don't remember much about PvE.
HoH is universal, you don't need certain expansions to see more players. You were probably in a bad timezone where not a lot of people were on or you were in one of the international servers which usually had less people.
I don't believe 65 plat. I easily hit over 130k and I wasn't a farmer because our guild only GvGs.
Yes you need Sigil, but the prices have been changing (dropping as time I checked) so I don't know the price now.
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