If you plan to tow extensively, I would highly recommend the OEM hardware over anything extra. The OEM connector only comes with a 4-pin connector, so you’ll need to purchase a 7-pin connector plus the aftermarket brake controller, but the OEM connector is significantly better designed, so it’s worth the extra cost.
The only other thing to keep in mind is that when pulling, you are required to use a minimum of 91 octane (or higher). However, it’s worth noting that if Climbing is important to you, then you’re free to run 87 octane all the time even when towing. But whichever Outback model you’re looking at will be more than capable of towing a 1,900-pound trailer.