Hi books, all going well with gd and pony, thanks for asking.
Some like to come in at night (our old pony, for example, who's fine and difficult to keep up to weight) The rest are best off turned out as much as possible, in my view. Horses which are stabled, fed hard feed and clipped need to do a lot of work, otherwise they can get a bit sharp!
Unless you need your horses mega fit I'd keep them out as much as possible. If you want to be able to still do a bit of faster work though you'll need to keep them reasonably fit so make sure that your midweek sessions include some faster work. I don't think it's fair to only canter at weekends, either keep them in moderate work or wind down (but this is a bit of a bugbear of mine as the woman I bought mine from used to keep her out (unclipped) in the winter and ride her once a week which was usually a fast ride out with a mutual friend on his big, fit hunter)
A good half-way is to rug now to limit coat growth, give them a low trace clip when they need it and invest in good turnout rugs for when it's cold, then bring them in if you need to overnight when it's very cold or wet, but they are both hardy breeds so I'd try not to mollycoddle too much, or you'll have fat horses come the spring. But there's nothing wrong with tucking them up in a nice cosy bed once in a while. That's one of the pleasures of winter
Re cuddles, some like it, some don't. Mine's a cuddler, which I love. She'll let you know if she's not enjoying it!
As regards hacking on your own, I really, really wouldn't do it as you're not very experienced and your horse is still green. I'm sorry, I don't mean to be harsh, but things can go very wrong, very fast. If you've got someone with you the horses are more likely to cope with the unexpected. If you're alone you need to be a very experienced rider to instinctively act correctly when faced with a big problem.
There's no reason why horses shouldn't hack out by themsleves, some are better than others, but it doesn't sound as though she minds too much and the more they go out alone the more they get used to it.