Hi Karl, welcome to the forum.
Our "starter boat" was a
MacGregor 26M. It was great on inland lakes and sucked on Lake Michigan (heeled to 25-30 degrees in a heartbeat with the slightest puff over 15 kts). It took just a little more than one season on Lake Michigan before the Admiral said, "Paul, we need a bigger boat!".
A couple thing we have learned:
The cost to buy/equip a boat is nothing compaired to the cost of
ownership. (Winter storage/summer slip,
insurance, electonics maintenance/upgrades, systems maintenance/repair (galley/refridgeration/water tankage/hot
water heater for the shower/the
head &
holding tank,
sails, the cost of running
rigging on a big boat was an eye opener vs. the Mac. The cost of a transcient slip for a 26 footer is a lot less than for a 35 footer.) Get the picture?
You will use your boat a whole lot more if it is kept in the
water (slip/mooring) vs. on a trailer in your back yard. We did keep the Mac in mast-up dry
storage one season and were able to be in the wet within 20 minutes of arrival with the tow vehicle.
Comfort features such as a
galley and bathing facilities are rare on a trailerable. Plan on coastal cruising eastern Lake Michigan from marina to marina where most have great bath house facilities and often have gas grills available for transcient boaters.
Start with the end in mind. If the first boat is really going to be a starter/trainer, then go simple (cheap as possible) and resist putting all the goodies on it unless you will be able to move them to the "next" boat.
If you have the time/resouces ... consider taking (with your girlfriend) a week-long
live aboard sailing course where you get to experience big boat sailing while living with three to five people. We had the Mac for two seasons before we took an
ASA 101/103/104
live aboard course thru
San Juan Sailing out of Bellingham WA. We experienced tides, tidal currents, sailing in/across active
shipping channels, nights on the hook, nights on a
mooring ball, getting in/out of a slip in busy
marinas and sharing the boat with an instructor & another couple. The
school boat was a 36 foot
Beneteau and we learned how easy it was for just two people handle.
Any sailing
books will give you the fundamentals. Check with your potential boat insuance company to see what boater
safety course(s) you can take that will get you a discount. Check to see if your local university has a sailing club. They often offer lessons and provide unlimited access to their fleet of
boats with
membership. (I started at the UW sailing club. They offered lessons and had a fleet of over 100 boats from sailing dinghies to 26 foot keelboats that I could use.)
Check out the local yacht club(s). Many have regular sailboat
racing with skippers often looking for crew. This will get you contacts in the local sailing community and get you on a boat with experienced sailors. This should let you ask the regulars why they do the things and helps you see the practicle application of what you read.
Welcome to sailing.