You'll run out of payload capacity long before you ever reach the meaningless and irrelevant max tow number. So keep an eye on that payload capacity listed on the yellow sticker on your B pillar. If you added any accessories after you bought the truck, those also reduce payload capacity. You'll be at the upper limit of your payload capacity, but you'll probably be OK.
Both my 2016 and my 2019 came out of Mexico. No problems with either one.
My truck is parked outside for right now, so I don't program the Homelink for just that reason. If I have a vehicle that's parked outside for just the night, I lock the garage door with the the lockout button on the wall mount opener. For easy access to my garage, I use a smartphone app that allows me to open the garage door from anywhere I have cell service. Something to consider the next time you replace your garage door opener.
I never take them up on their "free" oil changes. I've heard of too many oil change horror stories at dealers, jiffy lubes and independents. I do my own, so I know it was done right and I actually got the synthetic oil I paid for.
I ran mine down to Empty while driving through New Mexico. I wound up on a bypass that had me also bypassing all the gas stations where I had planned on refueling. I foolishly assumed there had to be a gas station somewhere up ahead. But as the gas gauge kept moving toward "E", I began to start sweating, as I was also pulling a trailer and I was gaining elevation, causing the remaining fuel to disappear even faster. Sweating profusely, I finally found the only gas station within 70 or 80 miles in either direction. It took me 23.25 gallons to fill up, meaning I was down to my last 3/4s of a gallon. I'll never do that again. In the future, if I have to, I'll turn around and go back
Interesting. I had mine installed a couple of months ago and have had zero problems. I used a learn tool that I got off of Amazon for $15. My next step would be to have the dealer reflash your truck's computer module. I'm assuming you have created a trailer profile and followed all the programming steps in the owner's manual, otherwise it wouldn't have worked to begin with. So, for whatever reason, your truck is dumping the retained memory every time.
If you plan on doing any towing or hauling, I'd pass on the Tundra. They have ridiculously low payload capacity and are best suited as an overpriced grocery getter.
I've had this problem too. I have found two things that work. One, I reverse the plug at the phone end. Two, I use the USB port in the back of the console. That one always works, although now you can't use CarPlay, which I only use for Maps, which is almost never. I also find that the phone charges if I turn it on after I plug it in. It's when I just plug it in that it won't charge.
I had the same dilemma as you. My primary objective was to have a tow vehicle with lots of payload capacity. I went with the LTZ over the High Country. I have the 6.2L engine and the Max Trailering package. I also have 1910 lbs of payload capacity. With a trailer that heavy, you definitely want the 6.2L and Max Trailering package. I would go SLT over Denali. 1485 lbs is way too little payload capacity for the size and weight of your trailer. My 2016 Silverado LTZ has a 1572 lb payload capacity and I overgrossed it with my 19 ft 5000 lb trailer. I do have a few add-ons that lowered my payload capacity a couple hundred lbs, but even without that, I was still pushing the envelope. And the 5.3L is a slug in the mountains. So don't listen to what the salesman has to say, even if your friend owns the dealership. They'll tell you that your new truck can pull way more than it actually can safely and comfortably.
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