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Clearly only a temporary fix.
This should have lasted longer, looks like you did a pretty decent job. This leads me to believe that the problems you are having with the frame and door are a symptom of a bigger issue.
we have a flat roof above it that drains off in that area, which is the root cause of the issue
When you say draining off; how exactly?
Is there guttering? If so can the downpipe be diverted to somewhere else (preferably another downpipe that drains into a soak away).
Without seeing the rest of the building it looks to me like the flagstones are a later addition. Given the age of the door and surrounding frame I'd expect to see some kind of quarried stone step leading up to it, slightly below the level of the threshold. By having the step below the threshold it protects the door and frame from sitting water. If you have a level put it on the flagstones, ideally it should fall away from the door with a very gentle slope, looking at the level the bubble should be "kissing" the line closest to the door, also use the edge of the level to check for hollows in the step (although if there are any you will most likely be aware of them already as puddles will form there). If the flagstones fall into the door they will need to be replaced.
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Bobbo
The door does stick a fair bit after periods of heavy rain. When I stripped it and re-painted a couple of years ago, the bottom of that side of the frame had completely rotted. I used a wire brush to get rid of the loose material, then fixed it and built it up back to a door shape with epoxy filler. Clearly only a temporary fix. The door and fame are massively exposed to the elements, and we have a flat roof above it that drains off in that area, which is the root cause of the issue. I had to do a similar bodge on the bottom of the panels covering the frames and the sill (see before and after photos from last time) although I did let in some new pieces rather than use filler for everything. The sill has now completely rotted again. It sits directly on top of the flagstones with no membrane underneath it. It needs to be completely replaced to be honest.