It's the same - for me - with making dungeons. Either I end up with a dungeon that looks like every other vanilla dungeon, or I end up with something so unbelieveable even I don't believe its a dungeon.
What you are supposed to do is imagine the area you are doing is real life. So why would a tower be placed, in a stronghold, at a particular gate or in a particular wall. What's it defending against, high ground, a road, a way in by river ... ?
... Same with everything else ... Does the fort need a handcart? Or a horse? If so, does it need a stable? If it needs a stable, where is the best place for that stable, easy access to internal roads/gates ... better outside the walls? Flowers right next to a well worn track ... unlikely, they would have been trampled, in real life ... better to place them a little bit further away.
It is one enormous big waste of time ... Or, very probably, the most fantastic thing you can be doing ... depending on your point of view
(so, as
they say, have fun!)
The most convincing areas are those which would make sense in the real world.