Does this have the 'trolley sleeve' to slide over my roller luggage handle?

It does not. There are pockets that do go all the way through, designed to hide all the back pack belts for easy overhead but I never used them. I just checked to see if you could use those on your roller but really don't think it would work. I will say that whenever I used this pack it's my only piece of luggage. Has a laptop sleeve and a place to keep a small pack rolled up for use when you get there or to fill up with stuff to come home.

Can the removable waistbelt be used as a shoulder strap to carry the pack?

No, the buckle is a different size. I don’t use the belt myself. I’ve never had the pack weight above 18 lbs.

What are people doing to combat no water bottle pockets on the sides?

Since it’s so cheap to buy, most are just carrying their water bottles in their hands, or get a bungee cord & secure it. Or, just throw the bottle away & save yourself the trouble. Of course, I’d recommend recycling. Too much water makes ya want to go, then you have to find a bathroom to go in.

Jacqueline, here in the United States, the majority, maybe even almost everything is made in the People Republic of CHINA. They have very cheap labor. People live in poverty there. They are happy with any monies from any cheap job. Please excuse my sarcasm. Although it’s well made. My daughter uses it for her constant airline travel. She’s never complained about it.