welcome! i'm relatively new to my GZ250 and this board but i'm extremely happy with both. i was in your same situation, trying to decide between the GZ, the Rebel, and the Virago. the rebel is definitely less tall-people-friendly. i'm 6' 185 lbs and i don't feel cramped at all on the GZ.
now obviously, the rebel folks are going to tell you the rebel is best and we're going to tell you the GZ is best so in the end you're going to have to physically sit on each of them and decide which one you feel most comfortable on. i think comfort is most important in this situation because all three bikes are pretty similiar performance-wise (not speaking from personal experience here, just what i've heard and read).
1. your father-in-law sounds like a smart man
you skipped number 3, so i'll skip 2
4. i get about 68mpg on my GZ. the gz has a 3.7 gallon tank compared with the rebel's 2.4 (i think?), so that might be something you want to consider.
about some of your concerns:
1. from what i've heard, and from sitting on a rebel, the GZ offers the best riding position for taller riders. but again, don't take my word for it.
2. outgrowing a bike is different than outgrowing a car. if you've never driven a car before and you get inside a (insert really fast car here) and stomp the gas pedal to the floor, you might crap your pants but as long as you've got enough road ahead of you you're going to be fine. on the other hand, if you sit down on a superbike and give it full throttle not knowing what you're doing, things are going to get messy, and fast. smaller bikes are recommended to beginners because they're more forgiving due to the lack of power; after you're more comfortable you might decide you can handle a little extra power and probably have a lot more fun. however, you mentioned you're not really speed-craving adrenaline junkie so you'll probably be perfectly happy with a 250.
4. from my experience hills can be a drag only if you're trying to maintain freeway speeds (65mph+), but other than that they are no problem. a 250 shouldn't have any problem at all maintaining 25mph up a good-sized hill.
i'll admit i've only been riding for a few weeks, so maybe don't put too much stock into what i have to say. just my thoughts on the subject.
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