2006 Ford F53 transmission and wheel bearing maintenance

I have a 2006 F53 chassis with the V-10 and five speed transmission. I'm at 66,000 miles. I'm about to head out on a ~3,500 mile trip and I just realized that I spaced doing my transmission fluid and filter change at 60,000 miles (I last did it at around 30,000 miles). The fluid looks normal but is a tad low (at the top of the "cold" measuring marks when at operating temperature).

I know this is a very subjective question but... anyone think I'm making a mistake if I top up the fluid and leave the change until after the trip? Changing the fluid before the trip would be a hell of a scramble.

Second question... the manual talks about lubricating the front wheel bearings, replacing the seals and adjusting the bearings, also at 60,000 miles. I have to admit I assumed the wheel bearings were sealed units and never noticed this in the maintenance schedule before now . I grease the steering and front suspension components but I've never messed with the bearings.

So, pretty much like the transmission... should I rush to try and have this done before the trip or just wait until after? I lifted the front end and checked for play and found none. I have noticed a sound for a while (several years) that's sort of like a medium or high pitch warble that seems more pronounced when turning. It almost sounds like a wheel cover but I know it's not that. It's not super loud but is audible at lower speeds. Now I'm wondering if it's wheel bearing related but I've never heard a bearing make a sound like that before. I do check the wheels with my hand at most gas stops for excessive heat but that's probably only going to detect a major problem with the wheel covers on.

Feeling like a dumbass for getting myself in this situation but it is what it is.

Thanks in advance for any and all feedback!