Heading to BVIs - Now what? :)

[SailorZman]

A pleasure to meet everyone. I'm a frequent sailor on SF Bay (Lagoon 380 & Beneteau 430) and am heading to the Caribbean next Feb/Mar to buy a boat and begin living my life a new way. I'm excited! As you know, much to think about and learn. Background info:
- Early 50s / single
- Experience sailing (SF Bay/some BVIs) / very social (do numerous theme events on my boats for fun (i.e. luaus, wine tastings, etc. )
- Budget for boat <$100k (I can pay more/but only if needed to support plan)
- Working on certs to offer paid charters/services

--> My question is about initial game plan & right boat to buy.
Options as I see them:

a) Just cruise the area for awhile (buy under 40')
b) take on paying passengers for trips (buy over 40')
c) start a weekly charter service (buy $150k+ Cat)

I hesitate to buy the Cat now when I'm not yet sure if that's what I want to do. Thus, I'm thinking about getting a monohull for under $100k - under 40' if I'm just going to cruise for awhile or over 40' if I think I might pursue a paying passenger/crew model. With a monohull, I'd just get to know the area, talk to local sailors, and decide that first year what I want to do. If doing a charter service excites me, I sell the monohull and buy the more expensive Cat.

Thoughts, questions, suggestions about revenue models & best boat for each is appreciated!
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