The Wrangler is really a poor choice for highway commuting. Poor handling, rough ride and lousy mpg are reasons why I say that. The Outback is fine for the highway, but not much for off road. If you are talking dirt roads, OK. But if off road is paths in the woods and unimproved trails the outback isn’t a good choice.
Before you make a decision look at a new Ford Explorer. The new one gets pretty good mpg, should be good for commuting and more room than either other option for family and hauling stuff from Home Depot. Not great for off road, but at least as good as the Outback.