OOC: Yeah, leaving the Underdark puts you in Quail Valley, by default. I actually meant where in Quail Valley? Pembrose? Bostwick? Whirtlestaffs? Twain, presumably to visit Magus Crus? The Abadoned (ex- hobgoblin) Keep to which the party now holds the Deed? Elsewhere?
You might want to think about investing some of your treasure toward recruiting a crew to improve the road to your keep, which would increase traffic to it, possibly leading to settlers, more population, maybe businesses, a growing tax base for the Lords of the Keep (The Party), etc. You might really want to think about NAMING the keep, too.
Sorry, I'm falling back to my original plan for this to be a LONG-TERM game, but it absolutely doesn't have to be one.
FYI: The D&D Next (5E) DMG appears once again to have the resources to support character strongholds and so forth, like 1E. Not sure if 2E or 3.XE did or not. I don't think I remember seeing that in 4E.
When we decide which way we'll go with the game, I'll open a new (5th) IC thread, and be sure that it's back in the correct Forum!