He'll have trouble since he's the clingy type. He'll do alot of walking the fence and hollering the first few days. He will quite down with time. He probably will eat very little because he's upset but don't worry about that. He'll get hungry enough to stop and eat normally in a few days. Make sure your fences will hold him or he will end up with the neighbor's horses. Not a good way to start off with the neighbors.
Instead of buying a 2nd horse, try to find someone with a retired pasture puff who is looking for a place to keep him. Ask at the feed store or put up an ad. Make them pay for their own feed plus $XX to cover the expenses of time, water, pasture maintenance, fencing... Trade for fencing, shed building, house/horse sitting... Try to find another gelding. He will be less apt to be joined at the hip with a gelding than a mare. There are also free horses everywhere looking for good homes. Many will be usable, sound horses. Check to see if there are any local horse rescues that you could house one of their horses on a temporary basis. You can always pick up a yearling for less than $100.