Viability of putting a boat out for charter

[jsc7]

In buying a boat I am considering the option of putting it out to charter. This decision could affect the type of boat I buy (and the kind of work I put it into after buying it). I am wondering how viable it would be to do this.

In my case the boat would most like be something like a 35-45 cabin cruiser that would be rented out for day trips or half days doing tours of the Boston Harbor Islands, maybe the occasional rental to somebody going to the Cape. I could also set it up for private cocktail cruises.

I don't need the money, and am looking to charter more to keep the boat in use and ship shape. I don't want to just use the boat now and then and have it sitting in a slip unused week after week. If I have a professional skipper working the boat, I see that as a way to keep it in good condition.

From the business side, I am a professional software engineer so I will have no problem setting up a web site to schedule the boat and advertise it, and will be proactive about advertising it. The boat will have its own web site. I am not going to just list it on a charter brokerage and pray, I will actively go out and troll for clients.

I don't mind doing a lot of maintenance. In fact, I kind of enjoy it. I am almost buddies with my car mechanic, I often hang out in his garage and we talk engines while he works. I do a lot of work on my car. I spend a significant amount of time in junk yards. Also, I love courtrooms and will have no problem at all dealing with damage to the boat from a legal point of view.

My questions are:

(1) Will it be relatively easy to find a qualified skipper that will be willing to run the boat part time, or is finding a good part-time skipper going to be difficult?

(2) Can I expect to get a reasonable flow of clients if I put the work into it, or is it going to be more like, work my ass off and end up renting it for only 5 days the whole season? (This kind of affects #1 above because I will not be able to retain a good skipper unless I have him working fairly consistently).