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I once had the same dilemma. I wound up buying the metal molding for front and rear and refurbishing my side rain gutters, and they wound up looking pretty nice. The metal moldings for my car (29 Tudor) are actually steel. Bending them to the contour was pretty tricky and even though I enlisted the help of an experienced body guy, it does not quite look factory. For the metal trim going into a metal drip rail (gutter), there is a tip especially designed for that transition. All the vendors sell them. However, if you are doing metal trim and transitioning to Hidem, I can see that you have a problem. Maybe you could modify the tips designed to go to the gutter and make it look nice enough.
I have seen lots of people use Hidem rather than the original trim. I don't have an opinion as to how water-tight it is, but presumably you can put sealer in the groove and make it pretty tight.
I understand that your car is a driver, and I can attest to the very hard work that goes into going to full trim and drip rails. It's a LOT of work. That is probably why we see so many done with Hidem. Not knowing anything about the condition of your car otherwise, the Hidem will be noticeable to those who have had the experience of doing it with metal. To anyone not familiar with the nuts and bolts of the Model A, they won't know the difference, and to the casual observer, the Hidem at least presents a finished look.