I don't think that you're going to get any meaningful insight from others - tolerance to cold, 'specially when it comes to extremities, varies quite a bit from person to person; some people "need" gloves at 60°F while others will go bare-handed at freezing or slightly below. This is one of those things that you'll just have to try, though I agree with the basic premise that winter shoes/boots are more convenient than booties (though I still haven't found a good winter shoe/boot for myself, unfortunately).