I think we are starting to get a better understanding of what the model is exactly. The 29 and your 30 were designed by different people so the fact that they have a similar look may hide the fact that there are subtle but important differences in the hull shape.
Jeff is very knowledgeable about boat designs and has worked as a designer. Since he has personal experience with Contests of the era of yours you should listen to what he has to say. One caveat, he has a much higher appreciation of modern designs than the traditional, but the reality is that for many people the cost of a modern, quality cruising boat is just not in the ball park so the question becomes, which of the older boats is best.
Some other comments, if your fiance is going to go offshore with you, she MUST be an active crewmember. There are no passengers in boats of the size we are talking about. We cruise in a 36,000 lb, 45 footer and there is still no room for a passenger. If she tries to go along to keep you company she will be miserable and so will you. If she does not want to be an active crewmember, find someone to go with you and have her fly to Bermuda - it is a great spot to visit.
I don't think they still make the Edson pump I mentioned - that is my I mentioned trying to find one used. If it were new you could not afford one anyway. They were close to $1000 20 years ago - but they do an incredible job. I agree with the comments about Whale pumps, the aluminum castings do corrode and the pumps are very pricey - the Hendersons are better since they are all plastic.
The trip to Bermuda can be totally benign or you can get the crap kicked out of you - it is totally unpredictable. It is not like the Southern Ocean and the chance of a knockdown is very slight at the season you should go - late May - early June departure from Lake Ontario is ideal. To all the people who say that Great Lake sailing can be just like offshore, it ain't true. I sailed on the lakes for close to 40 years before heading off and the conditions are different. The lakes can be terrible in November for example, but people aren't sailing then. On the ocean we have had periods of a week where the winds were never less than 25 knots and often more like 35 knots - you never get that on the lakes. Most people think in terms of one bad storm or squall, beyond that are the extended periods of fairly high winds and swells/waves in the 10 to 15 foot range.
Not sure what your budget range is, but there are some incredible bargains around. Saw in Gam that there was a Hullmaster 27 (Brewer design/decent build I think) for $2900. It may be a piece of junk but at least illustrates what a keen seller wants. Some people are still thinking about what they paid for their boat not the realities of the market - you just need to find the realistic ones. If you are considering an Alberg 30 or Contessa 32, I would lean to the latter with one warning - many Contessas were bought as hull and decks and finished at home and that may be a very good thing or not ... Also, headroom is a bit limited as I remember if you are more than about 5'10".