Painting over wooden relief

[Dace]

I failed spectacularly here as a noob trying to just paint over crappy looking parts on the first photo, should I just scrape all the old crap of with my painter's tool?
For the second photo can I just use caulk and paint over?

WIll be the last stuff to do. Thanks for all the help

 

[foxhole]

Replace the rotten timber .

 

[Odds]

Is it rotted or just coated in dirt/mould? Clean it up/strip it and fill any large gaps. Sand it, prime it, paint it. Sorted.

 

[opps]

I am guessing that there is a window directly above image #1.

If there is water ingress from the seal between the timber frame and the masonry sill, you need to deal with that first.

As a decorator, I expect the blown paint/filler to be either moisture ingress or powder based fillers that just delaminated (they often do that after a few years).