Stroller Rentals?

I haven't ever rented a stroller there, but I can tell you that they leave them around EVERYWHERE. I wouldn't worry much about standing guard over them, although I suspect renting them makes that even less of a concern.

WDW actually has a service where you can pre-pay for your stroller rental and they offer a slight discount (it's like $4 a day or something)..it's still expensive though.
That's kind of a conundrum. On the one hand they are expensive and bringing your own is probably more economical.
On the other hand picking it up on your way into the parks and dropping it off as you leave is MUCH easier than lugging a huge stroller on and off the buses or out of the car and back into your hotel..and then tripping over it all night long.
Personally, I would rent one. It's a cost but a cost I'd be sure to budget into my expenses.

As far as standing guard..well he'd be the only one doing it. Most rides have "stroller parking" and a CM is nearby. The rented strollers have your names on them (to avoid confusion) and as long as you don't leave anything valuable in your strollers you should be OK.

I vote rent. It's one less hassle and it removes any last vestige of feeling weird about someone pilfering it. (Even thought I'm pretty sure that never happens)

Either way, rent or own, make sure you never leave anything valuable in it and make it easily identifiable. There are some rides and attractions in WDW, where the cast members do move strollers to another location while you are inside. Think different entrance and exit locations. and strollers which were parked in the shade were then parked in bright hot sun and it spoiled some drinks which were in a "NOT" high quality cooler on the back of the stroller. Just something to think about.

Great advice. I think it's much more likely to "lose" stuff out of the stroller than the stroller itself.