As stated earlier, trailer brakes if installed must be operational in every state I know of. The Prodigy is the only controller I would recommend. Some vehicles already have the wiring harness connections installed. If not some dealers sell plug and play kits for specific vehicles.
Then I would replace the tires if they are 1999 vintage. Just make sure the load rating is adequate for your loaded trailer. Remember if you add a WDH later you will add load to the trailer axle.
As far as backing up any trailer teach your spotter to always be where they can see you in your outside rear mirror. If possible back up turning into the drivers side it is easier. If you can't see your spotter or are not sure of clearances stop and look yourself. I try never to blame the spotter for coming too close to anything because I am the driver. These concepts helped us travel for two years in a 38 foot toyhauler. Only clipped one stop sign in a campground.
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