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A less worrisome option is to put the FrontRunner on a trailer hitch behind the Penske and rent a bigger pickup to haul the boat. More expensive, sure, but overall maybe a better choice. I see those Penske/Budget trucks all the time hauling a car/SUV.
I'd stay as far north as you can then come down the plains. The I80 route to Cheyenne is your best bet. Not only is it less crowded, but its a lot cooler and a lot shorter with most straightaways out of WY.
I-80 to Cheyenne, then Denver, then Salina, then down to DFW.
I think your biggest worries should be the high winds once you leave Denver. The Plains in summer have a southerly fetch that can be 30-40 mph many days. The winds die down after sunset and do not get going until around noon.
If you plan to drive from 4 am to noon most days that will avoid the winds and any thunderstorms.
Get new brakes on all your stuff and test drive with them two weeks before for 100 miles.
To add to the things StealthRabbit, stillkit, and I have already said, here are a few more route options.
If you decide to take 287 from Limon, CO, into Texas, another option is staying on 287 past Henrietta to Decatur.
From there head east on US-380 it'll take you all the way to McKinney.
Before you get to McKinney, though, you'll hit Denton.
You can either stay on 380 and drive straight through Denton, or you can jog north on I-35 for a mile or so and take Loop 288 East around Denton. 288 intersects US-380 on the east side of town. From there it's a fairly easy 4-6 lane trek to McKinney.
If you take 288, be wary of the speed limit. I know several people who've gotten pulled over on that stretch of road.
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