Bottom line, in my fellow-newb opinion...go for it. It will be the best adventure of your lifetime.
See below for what little feedback I can offer. There are some great salts on this forum that can answer every question you throw at them. I ain't one of them...but I've learned a lot from them.
Hello and thank you very much for this great community! I've been lurking here and on another forum (where I am also asking this question) for the last few months and have read everything in the liveaboard area that appeared applicable to me. I've also read a few cruising books like "Sensible Cruising" that echo the opinions of many here.
I have a learned a lot (often gaining five new questions for each answer found) but I'm still having trouble putting together a final plan. But, having done my research, I feel more comfortable about asking for a little of your time in helping me decide.
Some info about me (I know this can be helpful in narrowing down options):
I'm 21, graduating from a New England University at the end of the month, and have been giving a great deal of thought as to what will be my next steps. I have a small but stable Internet-based company, and I want to take full advantage of the relocation flexibility this allows. I'm 6' 2", which seems to be no problem on most boats I've seen. I have been sailing many times but never for more than a few hours, nor have I spent the night on a sailboat. I have always lived in rooms under 10x10 so small spaces with limited storage/belongings in no shock for me. My goals for sailing are to eventually do a lot of coastal sailing to chase the ideal climate, visit family and simply making life more of an adventure.
My current plans are to take a sailing course (30 water hours) at URI as well as charter an overnight cruise so I can confirm this is something I am comfortable with. In parallel I'm trying to determine what would be the best plan assuming no unforeseen issues. I understand I'm leaping rather blindly but I'm fine with that. I know I would regret it if I didn't try (and frankly, nothing else seems as interesting - even if I eventually learn it isn't the life for me).
I know the below are loaded questions, so thanks for baring with me...
1. I'm currently looking at the 27-30 foot range, specifically the Catalina but have also heard votes for Hunter, Pearson, Alberg and Grampian. I've read of people living on 27s and loving them, and others swearing the 30 is worth every penny. I'm not convinced the extra ~1' beam justifies a 2x price (average of 10 cheapest Catalina 27s vs average of cheapest Catalina 30s on Yachtworld). My budget is flexible but I'm trying to get the right balance between spending less to own it sooner and not stacking the deck against myself. I would like to spend around $10k but can spend more if the trade-offs are worthwhile (the v-berth in the 30 is certainly far more attractive than the 27, but a line has to be drawn somewhere). If looking at the 30s, that budget will certainly have to be increased... I'd prefer to spend more on a smaller boat that is in better condition (again, I don't want to jeopardize my first experience by having to do massive rework on the boat from the start) then stretching my dollars for footage, if at all possible.
Totally depends on your comfort level with the bare necessities. I own a C27. I could have lived on it at one point in my life. I wouldn't now. No interest. I like comfort, space, and margarita machines. But that's me.
As you mention below, if you're willing, then it's all about location.
Also, whatever you do, just make sure it's a boat you can sail. DON'T BUY SOMETHING YOU HAVE TO WORK ON FOREVER BEFORE YOU CAN SAIL HER.
2. For a location I am thinking I would like to move south (perhaps the Chesapeake or Annapolis area) in order to make winters more tolerable and give myself more time to adjust and get a handle for everything. It would be easier for me to buy in the North as I can live with family until I find the right deal, but I could move south in a sublet or a good long-term rate at a hotel while I look around? While I really dislike humidity, I figure that until my sailing skills allow me to have better control of my environment, I'll be better off sweating to death than freezing to death. I'm really open to living wherever makes the most sense (given climates, boat availability, sailing attractiveness, liveaboard friendliness, etc.).
Dude...THINK! If you're going to move south, make it some place where bikinis are the norm. Otherwise, what's the freakin' point? SCREW WINTER! We're talking about sailing here. And if your business can run from Annapolis (when it's freakin' iced over), it can run from the Keys where chicks like being naked.
3. The one comfort I would like to have is a working shower. If I'm in the north this would really need to be indoors, but further south I imagine I can use one of the 1-2 gallon bug sprayers in the cockpit during most months. It doesn't have to be piping hot, or necessarily long, it would just, to me, make it seem more like a home and less like camping. I would really prefer to ween myself out of the marina (hook or mooring) as soon as possible (to reduce costs and encourage mobility), so relying on one for showers is a step in the wrong direction. I've heard of someone making a shower in a Catalina 27, and the cost savings of going with a 27 as opposed to a 30 could free up some funds to have some custom work done to make a shower possible? I'm still not sure if this is something I should just forget and use a marina shower or stick to my guns and make something work on-board.
The chicks I mentioned above? Solar showers in the cockpits. Think about it.
Since I live in a somewhat semi-tropical climate, no way would I put a shower on my C27. Mildew is out of control enough. On the other hand, if you're on you boat in January in Annapolis in a freakin' snowstorm, I could see the appeal.
I know my questions are very subjective, but I appreciate any help you can offer! Learning from others can save a lot of headaches and expense.
Sailing is about adventure. Go have one!