Up until you brought up Wake Is and HI I was ready to recommend boats like the Brewer 40 PH, Sceptre 41/43, Cooper 416 as good cold weather boats often with inside steering stations, as do most PH boats. Still appealing, as there are measures you can take to protect larger windows for off shore. The Sceptre's windows are less of an issue than the other two and I think it would be a pretty good candidate for what you're planning.
Here's an example:
1986 Sceptre Aft Cockpit Pilothouse Cutter - Boats.com
With a bigger budget I think I'd be looking at Ovni or Boreal for the ultimate in higher latitude and adventurous sailing.
Here's an example:
1986 Sceptre Aft Cockpit Pilothouse Cutter - Boats.com
With a bigger budget I think I'd be looking at Ovni or Boreal for the ultimate in higher latitude and adventurous sailing.