1. Depends on what kind of roses they are, but likely they'll be fine...
...there are a few heirloom tea varieties that will not tolerate much cold, but if you're in a place that gets snow, likely you wouldn't have bought them. Keep them from freezing or drying out in dessicating winds and they'll get by.
3. Some companies will let you specify a delivery date, but you have
to order pretty soon. Alternatively, buy some potted roses at your local nursery and keep them well watered until you get a chance to plant them. Over the years, I've had about the same luck with mail order bare root and potted roses. I just use mail order because of the greater variety available.
I'm pretty sure Jackson & Perkins has a contract with the United Farm Workers; at least they used to.
Heirloom Roses are all self rooted but they ship a very small plant that will take a year or so to come up to size.
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