Here’s a question for the sake of curiosity.
Has anyone ever put a room request in that was above your current room level? For example, requesting a water view when you have only paid for a standard view? If so, what happened? Did you receive said water view or did they “haha”, tear up the request and give you the most horrible view ever?
Just curious.
lol
“When my room started with a negative sign I should’ve known but when the key came with a flashlight attached…”
I don’t recall hearing of anyone who requested room features outside of the class of room that they reserved and was successful. The conventional wisdom is to make sure that your room request is in line with the class of room you have and not request locations, views, bed types, etc. that are not available within that class, as you risk them ignoring your request altogether rather than try to find a room based on just the legitimate portions of your request.
Love your handle. 
I agree with @brklinck. While I’m sure there have been some successful attempts, I would ask for the best room you are eligible for. Otherwise if your request is ignored, you could actually get a worse room than you otherwise would have.
That said, when you check in it wouldn’t hurt to ask.
Twice at DL when we checked in we were upgraded. I think it was due to our first time at that hotel. DLH and then GC. Both were fabulous upgrades and greatly appreciated.
Oh… one time I did call to fuss about our room at FQ… I had paid extra for something but was looking at a parking lot. CM asked, “Is there green between your window and the parking lot?” I responded affirmatively and they said they met the requirement. I replied that was bogus and scored a discount on my room.
I’m laughing at the logic. LOL
This, most definitely. Plenty of examples of pixie dust being sprinkled when people ask if there is any chance of an upgrade when actually checking in. Including one of my own. 
I just have never heard of this happening as a result of an on-line or faxed room request.