Hi Adam, you've got a lot of good ideas here.
My husband and I draw from our 8+ years / 50,000+ miles of cruising around the world to mentor people and help them get "out there" too.
This ranges from information on how to prepare, assisting with
boat selection that meet your needs/plans, evaluating listings, the pros/cons of different
gear decisions, and just a good ol' reality check on any questions youhave.
More information about our Cruising Coaching here:
Personal coaching: ask the cruiser | Sailing Totem
Happy to field questions,
Behan