Where I live there is a boarding stable literally 5 minutes down the road, but instead I board at a place that is 15-20 minutes away. The close place is huge with a few arenas, lots of trails, and lots of people. My place has a lovely indoor arena, but a large portion of it is currently taken up by hay. No outdoor arena, but there is a big field with jumps, and a couple of miles of trails. My big thing though is the quality of care. At the nearby place the care is sucky, and I have heard of many horses having big issues due to it. They also have silly rules about arena usage and the like. I chose the far away place because of that.
Were I in your situation I would almost certainly move to the close place. Not only is it close, but you know that your horse will get appropriate care. Are there empty paddocks that you can ride in? A large pasture? Like I said, our barn doesn't have an outdoor arena so we just put jumps out in the big back pasture. I may pass if there were NO open and available areas for riding, but sometimes you just need to get creative! I would imagine that in your situation it may be worth it to trailer to trails since it is so close, and you have a trailer at your disposal.