I thought someone on a tour said the boat was back in Lorelai's garage. (Take that however you want!) If they are using that in the show then I could see almost daily contact with L&L. Her driving up and him working and a few words are exchanged. Or warm spring nights with him outside her house...
Lots of progress can be made with a few words at a time. It would be private place to talk but yet the boat would be a good excuse so that it isn't about them.
We know Luke has to move the boat and that he will be fixing it up for the summer. Seems like Lorelai might offer her garage.