I can’t comment on Austin roses as I don’t grow them. Compared to most OGRs and moderns, I’ve found Austin roses to require significantly more water to grow and flower. Living in California, water is a prime consideration. Add I’ve not found them to be AS resistant to the mildew and rust issues which are our most prevalent fungal problems as many OGRs and moderns I’ve selected and work with. If you’re interested in using Bathsheba, try it in both directions with different mates to see if it works better with some compared to others. Some roses simply won’t set seed. Some set seed which refuse to germinate. Some can be very picky concerning which pollens they will accept. The only way to know these answers is to try it. Good luck!
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I have many of the same issues with winter that you do: I have also found early summer cuttings to be best. I have done late season ones that I kept inside under grow lights half the winter before letting go dormant and moving to the garage. (Ones kept all winter under lights tended to fail in spring when they should be starting to grow.)
In your zone 5 as long as possible is usually the answer for hip ripening, although some years can be an exception. Potted plants in and out, or in heated garage with lights is a great idea for late season to buy more time.
Another thing I have done that seems to help is to cut hips as one would take a cutting and put it in a vase of water, just like a cut rose. On the window sill these will continue to ripen; I can usually buy a few weeks this way. I have found that hips cut far too early will still fail. It seems to work with those that have had almost long enough, but just arent starting to ripen yet. Whether this actually helps with the seeds inside, or just helps ripen the fruit on the outside, I have no idea. But I have had many seeds germinate from this treatment.
Another option is to take hips on cuttings (as in previous method) but then remove the leaves and place in a ziplock with just a few drops of water. Works much the same as the other method.
Obviously any hips requiring a good bit of time still would be better on plants in pots to use the other methods.
My suggestion would be to select plants for cuttings and other plants for breeding right away. You could then try breeding the cutting plants also in the 2nd flowering. But you would at least have some hips from the 1st round that get longer ripening period.
Have fun!!!
Duane