Greenfield vs. Brownfield is an interesting debate.
Going the upgrade route (brownfield) is fine for many and retains perf data and the like (if requested to). I've found it to be straightforward in a majority of cases.
New instance (greenfield) allows you to redesign (and rid yourself of those design decisions you [inherited|got wrong the first time]) but you loose perf data (but keep it in vROps).
Personally I prefer the latter greenfield approach as it usually gets a 'better' architected solution at the end of the process. There's *loads* of excellent (free!) resources out there to help you with both approaches.
Above all, get off windows and onto the appliance. :-)
p.s. Check your DNS (forward and reverse) is right. No, actually check it. ;-)
(Disclaimer: I work for VMW)