Ok, so to prove I'm NOT crazy and that I DO know how to play this game...
I ran into this problem again tonight! @@
Thankfully, the evidence is still here though.

If you could be so kind, take a look at my planes. I have a HS121 Trident 1E-104 that I want to fly from Toronto to Bogoda. The distance, according to the premium gate search feature is 2230 NM. A trident 1E-104 has a range of 2443 NM. The trident I want to use has 24 hours left. I already have a gate rented at Bogoda too. Why I can't make the route is beyond me (hence I suspect a bug).
Here are some pictures to prove I'm not making this up, nor am I crazy!




Please take a look at this when you get the chance and see if you can figure out why this is happening. @@
Gisa ^^