Pasture boarding

I'm going to be leasing a 4 yr old Appy soon, who has just been started under saddle. He is really sweet, and almost completely bombproof. I have ridden him twice, and I love him. My question is here:

I will be boarding him at a farm, where he will be in the pasture 24/7. He is usually kept outside. The place that I am taking him to has an outdoor arena, and some sand paddocks, but nowhere to ride him inside. I will only have him from september, through the winter. I was wondering if this is an ideal place to keep him. He likes being outside, and is never kept inside. The owners want me to train him, and start him over fences. I just wasn't sure about riding him outside all the time.....

My only other boarding option would be at the current barn I ride at, but it is up for sale right now, and they may be moving partway through the winter. I don't want the horse to be put through having to move twice.

What do you think?????

It can never be emphasize enough how important access to a pasture is to a horse. Horses naturally make their living wandering and grazing, and spending too much time in a stall or even a paddock can cause them to have behavioral problems.