Value of boats based on age, use and location

[pygmalion05]

I am looking into getting my first sunfish (two, actually) and I am trying to figure out how to go about it, since I am in an unusual situation. I live in Puerto Rico and used boats are not plentiful, and so far are priced way higher than in the US. Here are my current choices to get two boats:
I can buy two 1998 sunfish from a sailing school. They come with a trailer and a dolly. Everything is very used, but completely functional. The boats have obviously been sailed a lot, but are in good working order, even if they do look a little beat up. There is evidence of many small repairs that were done professionally. The sails are a couple years old. I have sailed them and they seem to be fine. I haven’t weighed them. The seller wants $5500 for the whole package (two boats, a dolly, a registered trailer that will hold three sunfish and two kayaks).
Option two is to buy two separate older sunfish and modify a trailer so I can tow them together. They are both from the 70s, I believe. One appears to be in very good shape, though I haven’t weighed it. The sail has a couple small patches. It has what appears to be an aluminum rim around the edge of the deck. It has a hiking strap and a retractable fiberglass rudder. I don’t think it has been heavily used and has been kept covered, at least for the time the current owner had it. $1500
The second boat doesn’t have the aluminum rim. It looks more like the newer boats, but it wood rudder and daggerboard with a wood extender. The rudder doesn’t retract. It is in decent condition, but shows some wear. It was previously a sailing club boat, but was bought and had some restoration work done 8 years ago. It has not sailed much in those 8 years. It has been stored upside down outside. The sail looks old and I would look to replace it before long. I haven’t weighed it. It comes with a trailer that needs a little work, but could be modified to hold a second boat for a few hundred dollars. In the mean time I could put the other boat on my roof rack when I transport them. $1400
So option 2 totals $2900, but needs a new sail, some trailer work, and I would need to buy a dolly, which may be hard to find.
Option one is $5500 and is ready to go with newer, but more used, boats.
Am I nuts to be considering either option? In the states it seems like I could find option 1 for half the price or less. However, it apparently costs around $800 and a lot of work to get a Sunfish to Puerto Rico. Option 2 is more affordable, but the boats are much older. How much should that matter? I will be using these boats to teach my kids to sail, so I’m not worried about looks and performance that much.
Finally, if anyone knows a way to get a couple good boats down here at a better price, I would love to know about it.
Thanks in advance!

 

[Wavedancer]

I suggest you contact the local Sunfish fleet captain (or captains) and/or the ISCA representative.

ISCA-Puerto Rico Region

Sunfish Class Association

www.sunfishclass.org

 

[LVW]

With the $5500 package, you'd get your dolly, decent sails, and can recoup some expense by selling one trailer. If $5500 is the "going rate", re-sale shouldn't be a problem.

Stateside purchases risk having fiberglass repairs ahead, (although easy and fun) sound like some "work" you'd like skip.

Make sure the boat is a genuine Sunfish. The Sunfish on the sail isn't the threshold of identification! Parts are seldom interchangable (or even available).

 

[Oldfish newfish]

I'd go with the two complete boats.
It's more money, but if both boats can sail immediately with reasonable reliability for a year or two, that's what you want. I bought one that needed "a little TLC", and spent a month grinding, glassing and growling, spending some nice sailing days, tearing out shoddy repairs and chasing obscure bits.