I would have a good look at what the competition are already doing (Google and real life, from a bit of dock
walking and enquiries as a potential Charterer - if something grabs your attention I would think about going out on a Charter)......plus I would look to buy an existing Charter Operation in your area and / or the level you wish to pitch
at. Not neccessarily to buy an existing operation - just to suck as much info out as possible (accepting that you will be told a lot of BS, but will be nuggets amongst the dross). Timewasting? Well, if folks can't take a joke are in the wrong business......besides, you may stumble accross a deal that is worth considering.
I would also bear in mind that everyone has different ideas as to what "luxury" means (Punters and Suppliers). sometimes very different! For some it may mean a bucket each
- others may require a constant stream of smoke blown up.......
For me the fundamental thing is that both of ya can cope with Punters 24/7, IMO having a tolerance level high enough is not something that can be learnt - apart from the physical capabilities of the boat (gold plated toilet
roll holders etc) and the experiance (sitting under palm tree sipping cocktails etc) you are most importantly selling yourself, in mind, body and spirit - often at the cost to your soul! The Hosts can make or break an experiance, appreciate that likely most of 'em won't be coming back - but you want them to say nice things about your operation......the "challenge" is that every Punter will expect something different from the hosts, from doing SFA for them to wiping bums 24/7.
Appreciate that bigger is very likely better (esp. as luxury don't usually include 7 onboard sleeping in padded locker space) - but given where you are, why not try out doing Charter on your current
boat, even if not at the "Luxury" end you envisage for later (sell the business - but keep the house?) and if that shows potential then go for the bigger boat. and if not, you still have a boat that suits your personal needs whilst you whistle up a Plan B.