Domestically I see very little difference in executive level rooms and standard rooms. Lounge access is nice and I'm usually happy with that even if my room is not actually on the executive level.
That said, I've had a pretty good upgrade percentage, around 50% of my upgrades are more than a view (could care less what's outside the window) and of those upgrade, about 20% have been to suites or similar. I've had 2 upgrades to flagship rooms (Towers Suite at Hilton MIA, President's Suite at ES Atlanta Centennial). There have been times I've been disappointed (usually at HIs where I know there are suites available but I only get a "Study") but more times than not I'm very happy with the upgrades I receive.
Now, just because I've been somewhat lucky with upgrades over the last year doesn't mean I'm opposed to some investment in re-valuing the Diamond program. I envision something like 24 hour space-available Suite upgrades for Diamonds, 2-category excluding suites for Golds, and 1-category excluding suites for Silvers. More than anything, some constancy across properties would help. Some HIs refuse upgrades entirely even when available... make them work within the system or pull their franchise. Also, confirmed points upgrades would be great... seems like an easy way to get folks to spend points even on a paid stay. There are times when I would gladly pay the standard room paid rate + the standard room points rate for a confirmed suite.
Also, allowing upgrades to 2-bedroom suites at ESs would be a nice touch... there are times we travel with friends who aren't very well off and we usually chose an ES and let them sleep on the couch... an upgrade to a 2-bedroom suite would make those trips alot more enjoyable, especially for our friends who we want to help enjoy some travel a bit outside their own means.
A lot of these enhancements would require an overhaul and standardization of the room class system. It would need to eliminate some of the over-classing many properties use to work the system (+1 class for a view, +1 class for a balcony, +2 class for a view w/ balcony, ect). It would require no more than a +1 class bump for a substantial change in view (ocean vs. garden) and everything else be based solely on the room itself (mainly size, possibly renovation if substantial). It seems the hardest part would be making all the properties and (owned and franchised) to adhere to these policies.