Is this too small? Or should i stay over 16'
Weighing a few factors here:
Distance: Given the number of boats that are NOT in your area, the Hobie cat (if that was the model) that was somewhat local, vs this one that is 327 miles and 5hr 32min away (more time due to the really small wheels, and who knows what the bearings are like), or 10hr to the Minneapolis area, there aren't exactly a lot of choices, are there. And ... the summer is wasting away.
Trailer tires: For any older trailer I'd be concerned about towing a long distance with older tires. Sitting out in the sun is not helpful. Research of tire ratings will provided maximum speed, and then there are the wheel bearings to be concerned about.
Boat size: Well ... it would be doable. Maybe I would say "might be doable". This depend a lot on ones agility and propensity to comfort. For the kids and teens at the Royal Victoria Yacht Club in Victoria, BC, this would be a perfect two person boat.
Grownups: Hmmm.... for me it would be *kinda* okay. I'm sure my wife is older than yours, not as agile anymore, and for her it would be a dealbreaker. As they say, "Your mileage may vary."
Swimming ability: What a difference a few feet makes. For us we would consider this more of a sport boat, and, our water never really warms up but you say your lake isn't necessarily that cold this time of year. Still, capsizing it then trying to climb back on could be a challenge for some, especially with two people. I would hate to swim with a lifejacket on. Definitely a human-ballasted boat and tipsy. For only 2-feet more the Catalina 16.5 would be a lot more boat.
Young, or young at heart: As we get older there can be a tendency to underestimate our abilities and endurance. It's been mentioned above about the importance of having the significant other on board and this would be a prime example. While I agree with the Hobie cat being a sport boat, in some ways this will be just as much of a sport boat. This would be a better boat to learn on; HOWEVER, given the distance, the cat being a lot closer, could POSSIBLY be an equal or maybe even a better option for two who are planning to be Seniors. Having said that, one option might be to get something like this for yourself for this year. Heck, what's $1,000??? Easy to launch and retrieve, good for this year and into next year, resale value, even if sold for $700 or 800, wouldn't be a bad for learning costs. It'd be a somewhat good learning platform for sailing solo but doable for two who still have some athletic abilities. This might be a boat one could use hiking straps on for human ballast.
Personal opinion: While it *could* work, my guess is it would be mostly your boat, but then I don't know either of you. A 16-footer like our old boat would be okay because it would be comfortable with freeboard, cockpit combing, beam for being less tipsy, easy to single hand even when two people are on board because the main sheet and jib sheets would be out of the way. The boom clearance would be a bit more. This would not be MY first choice but a 10-hour drive (one way) is a Looooong drive. Plus, crossing the border with the registration might be a problem. Would not want to be bringing back any invasive species, either. Lots of room for thought here.
EDIT: Just after leaving my post I went and looked on Youtube and there are lots of Capri 14.2 videos. I was unfamiliar with this model and just looked at the picture and it looked more flush-deck So, actually, instead of re-writing my post, it appears this *could* work for the two of you. Not perfect for someone approaching retirement maybe, but with the warmer weather right now and the options available, and the planned time frame, it could be money well spent to start learning on and get the feel. Having a large lake there would be helpful for resale, I would guess. Don't know where the prevailing winds come from, probably straight down the lake? Would be nice to have some beam-reach winds. So, probably not the best option but not necessarily that bad. Wet, yes.
Check the condition of the sails, if they are "blown out". This is all about learning about boats, right?
Edit #2: Just did some Craigs list searches and in the Seattle & Portland area there are two 14.2 boats for $2,500 and 2,800. Detroit MI $2,200 and $1,900, and a dealer boat for $3,000. Naturally age and condition are important. One thing I like about the boat in your picture is there is no bottom paint so it was dry-sailed. I'm surprised they're going for that much but new boats are expensive and they might not be that old.