Siege definitely has issues.  Things I would like to see:
* Automatically record win/loss ratio per map.  After 30 recorded rounds (where player population > 50), if defenders lose > 70% of the time, decrease the map timer by 30 seconds, wipe the records and start recording win/loss ratio again.  If defenders win > 70% of the time, increase the map timer by 30 seconds.  Map time will now be a function of the map.
* If nobody is on a player built ladder, you get a "Drop Ladder" option, which destroys it, same as map ladders.  This will address the issue of hard-to-hit ladders (especially for people with short weapons).
* When a deployable dies, it deals damage to all other deployables immediately around it.  This will address the issue of people creating big piles of crap.
* Fix the first round door bug.  Or subtract 1 minute from the first round of every map.
Maybe after Strategus reaches a stable state, we can see a little more love on siege.