If I were in your situation, I'd do exactly what you suggested; regear, add a brake controller and maybe airbags if needed. A trailer that size is going to need a weight distribution hitch anyhow so the air bags may not be needed. This would be a lot cheaper than the depreciation hit you'd take if you traded in on another Sub so soon. Do some research and see if there's an existing plug-in under the dash for an aftermarket brake controller. This would make it much easier to add one. My 2008 Silverado had a harness tucked under the dash to connect to the controller then a fuse was added to the correct place in the fuse block.
If your Sub is 4x4, you will need to regear both front and back but that shouldn't run more than $2500 at a reputable shop, maybe cheaper if you shop around. I had my 2010 Wrangler regeared front and rear for around $1400.