The solid teak tiller is being epoxied/varnished as I write this. The rudder shelf, which will replace the convex seat hatch, is built and is being expoxied/varnished. It will hold the Tides rudder bearing which is, as you say, a belt and suspenders approach. I think a bronze plate and bushing would do fine otherwise. I'm just an overbuild guy. I've also found a Vetus fiberglass tube that will work perfectly to enclose the rudder stock between the deck and the shelf. We will be fitting all of this together in the next week or so, depending on the weather. It rains a lot here.
I personally don't think it will hurt the resale value of a 34. I have seen people who plan to bluewater cruise actually looking for tiller boats. And, judging by the number of people on this forum who've expressed a desire for a tiller over the years, I think there's a market. I, for one, would have paid a premium for a tiller boat when we were looking. Just couldn't find one. In any case, we are willing to take the chance so we can enjoy our boat more fully. Having said all this, I would never try to talk anyone into converting. We have our reasons and are willing to share them, but in the end, it's an entirely personal decision.