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The travel during that time should be okay. There are several routes west starting with I-90 in the north then I-80, I-70, I-40 and I-10. Any of those routes are good during that time of year other than maybe some rain in the northern routes. I-70 and I-80 are the most mountainous if I recall with I-90 a close third. I-40 isn't so bad but there is at least one gradually high point around Flagstaff. I-10 is the flattest but can be the hottest.
The Montana will be a more sluggish tow than the Cougar but it also depends on the TV you used especially when you're climbing hills and downshifting on the descents. I am only talking about the Interstates but there are a zillion suitable two lane roads but you just might get surprised on them by some unforeseen climb or such.
If you have towed a Cougar to Alaska, I'd say you are experienced as long you did not over do the traveling and did not have any difficulties associated with rushing things.
In your other post it sounded like you have a suitable vehicle and it's well-maintained, then you should have no trouble taking any of the Interstates through the Rockies. Just don't expect NASCAR-like speeds and performance - take your time. Your experience traveling to Alaska should give you the same roads and conditions of what to expect except that the Montana is heavier! Be careful of your tires, keep the psi perfect and even consider a TPMS just in case something bad happens with the tires it will help notify you immediately to lessen damage and get you to pull over sooner. Otherwise whatever you did when towing the Cougar should be pretty much the same as far as driving is concerned. Allow more time for braking and keep the turns wide. Avoid cutting curbs especially on right turns.
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