My partner stays there often when in Belgrade. Experience is similar to yours. They do give him an upgrade every time as both Gold and now Diamond. However, during last two stays it was always a push during check-in. A couple of months ago he was given an upgrade to Junior Suite which is more of a corner room then a suite (he knows as he stayed at a proper suite). I guess they tried to trick the system. Also two times they failed to award correct amount of points. They had it in the system that they award 1 point for $1 spend. So it was a long process to get it a corrected. I don’t think hotel understands Hilton Honors loyalty programme at all.
He previously stayed at Metropole and Hyatt. Metropole was better, but he hasn’t stayed there in two years so no recent experience. Though at Metropole they were much better at upgrades, often two categories up.