Is this the best way to finish the eave sheets to brickwork and window tops?

Hi all. I'm trying to tidy up this place which seems to have a myriad of diy disasters around it most of which I have terminated but I'm not really sure if I can fix this one for good or if its completely normal or something I have to dream up something better for.
The issue is the eave sheets are not dead flat and so gaps appear between the timber dress strip attacked to the brick work and the eave sheet. The previous owner filled the gaps with caulk and in doing so put white caulk all over the timber dress strip put blops of caulk her there and everywhere and made it look all together poxy. I have cleaned most of it off and now I'm a little flustered as what to do. I know the norm on a BV is to use 19mm quad and paint it white. I cant do this as the bricks finish lower than 19mm below the eave and there is teh issue with what to do above the windows.
The solutions I have thought of thus far.
1 Caulk up and paint white (I'm thinking this will look crappy above the windows?)
2 Put a small quad and paint white in front on top of the timber dress strip. ( not sure its a good idea though and fixing it will be a problem as the existing timber strip isnt exactly rock solid (being nailed into brick mortar and liq nails onto brick most of which is no longer functional.
3 Retain as is and restain and clear coat timber dress strip and reattempt caulk of gap between dress strip and eave
Any help with this one would be awesome.
Its not that bad a house but the finish on this item is just crappy at the moment and I want to make it completely unnoticeable as it should be.
Heres some pics. I'll remove that diy joiner in shot 9 when I get to it.

http://www.renovateforum.com/attachm...224_154537.jpghttp://www.renovateforum.com/attachm...224_154545.jpghttp://www.renovateforum.com/attachm...224_154556.jpghttp://www.renovateforum.com/attachm...224_154559.jpghttp://www.renovateforum.com/attachm...224_154759.jpghttp://www.renovateforum.com/attachm...224_154810.jpghttp://www.renovateforum.com/attachm...224_154822.jpghttp://www.renovateforum.com/attachm...224_154831.jpghttp://www.renovateforum.com/attachm...224_154838.jpg
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