Mitch,
I purchased an '83 O'Day 19 two years ago. It is a downsized version of the O'Day 22. (The O'day 192 and 222 are model upgrades with more space under the cockpit for the berths.) I paid $1600 on eBay from one of the charity auction sellers. I was confident that at the price (and the condition viewed in the photos) that I would be able to handle anything that might be wrong with it. My wife and I have sailed it the past two seasons Boston Harbor, Portsmouth Harbor, and Lake Champlain with very minor "adjustments".
It started life on the Hudson River then was given to new owners as a wedding present by their uncle. They have a cottage just north of you in Pocasset and were tired of waiting for a mooring. In spite of the fact that they could see the town launch ramp from their front door and the O'Day was on a trailer with rollers, they never put it in the water. So they donated it to a charity organization that auctioned it on eBay.
So COST can be VERY reasonable. Trailering means I can go anywhere.
Once we were caught at low tide in Little Harbor (Portsmouth NH) using the Odiorne State Park launch ramp. We motored up the remaining little channel (using an electric trolling motor) to the lauch ramp. The concrete portion of the ramp ended well before the low water mark. We could have waited a few hours for the tide to come back in, but instead backed my Jeep to the end of the concrete, unhooked the trailer pushing it into the water but tethered to a strap. Since the trailer had rollers, we could winch the boat onto the trailer with little effort. The Jeep in low range pulled the boat and trailer up the mud to the concrete area. The only thing I wished I had then was a wheel under the trailer tongue.
PROS:
This model (O'Day 19) has a swing centerboard and a short weighted keel. Draft is 12 inches. I could launch anywhere, beach anywhere. It weighs 1400 lbs and can be towed by most vehicles with a type II rated hitch. My Jeep looses only 2 miles/gal on the highway when towing.
The cockpit is large enough for four adults for a day cruise. We did this often. Sleeping arrangements are "camping for two". Since we day-sail, this was never a problem. The cabin was for storage. But for watching the fireworks from the water in Burlington VT, we comfortably had six adults. But most of the time, I enjoyed either being by myself or with my wife. One can be social or seek solitude depending on the situation.
The trailer can be a simple one readily available for motor boats. Keeps the cost down. Go with rollers if possible.
The boat can easily be propelled by a small outboard or even simpler by an electric trolling motor. Choose by your needs for wind and current. I alternate depending on the location.
I can single-handedly raise and rig the mast with no special assistance. I use the jib halyard and walk the mast up. I'm 57 and in "average" shape for my age.
CONS:
Size - overnighting would be like sleeping in a tent. I can do it, but there is the "Admiral" who prefers a real bed - it's actually mostly for back support reasons.
Fair Weather Sailing - my wife is not yet comfortable with the rolling motion when the winds are above 15 knots. The keel weight of the O'Day 19 is not considered self-righting. So it is best as a fair-weather boat when the crew is inexperienced.
FOOT-ITIS:
The 19 foot size is very good and convenient for someone who wants to primarily day-sail and be able to go anywhere at the spur of the moment with up to 4 people. Overnighting is like camping.
In August, my friend (he and his wife were our regular sailing companions) purchased a '73 Ensenada 20. Amazing how much of a difference one foot in length and different layout will make. They ARE very much a couple who would overnight in the boat and are our age. The interior of the boat needed significant repair but well within my friend's skills. He also modified the insides to meet his needs.
This October I purchased a Catalina Capri 22 (wing keel) from eBay to address the needs for a little more space (for socializing) and stability with a fixed keel. The original owner had died. His friend received the boat but was not an active sailor. It was donated t a charity and auctioned on eBay. I got it for $1400. It had no trailer but I modified the one for my O'Day to get it home. Condition - ready to go back into the water.
OBSERVATIONS:
Pulling it back from New Haven CT to southern NH went very smoothly. It weighs 2200 lbs. The keel boat (2' 8" draft) sits up higher but most of the weight is in the keel. I will be reworking the trailer to lower the boat and reattach the rollers.
The experience we had at Odiorne State Park launch ramp convinced me that I could launch and retrieve a keel boat from my favorite launch ramps (but not from Odiorne's ramp). Yesterday I checked out the ramp at Dover Point on the Piscataqua River near Great Bay during low tide. Yes, I want those rollers back on!
SUMMARY:
Within your price range, you can purchase a reasonable sailboat, trailer, and motor. The more work you are comfortable doing, the better the deal you can get. My two boats needed basically to be cleaned because they have sat unused for a few seasons. But other than replacing a fitting or two, both were ready to go into the water the day I picked them up.
Boat yards often have boats that the owners have "abandoned" and stopped paying the yard fees. Often, you can get a very good deal assuming the yard owner has gained possession of the tittle.
EBay has worked out very well for me. My friend found his on Craig's List. He is happy.
If you are unsure about your "repair" abilities, then by all means look for a boat using a registered surveyor.
AND YES, the Admiral has stated that the O'Day 19 be sold this Spring (a pre-announcement in case anyone might be interested). I still have my Paceship P-17 for those "thin water" lakes...
John