Two storey wrap around extension - right to light

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Currently in process of working out plans and getting them drawn but to try and limit wasted effort I'm trying to work out best way forward.

Current layout is we have a 3 bed detached house, prior to us buying there was a full width single storey extension built some years back with full planning. Right hand side is the boundary, left hand side we have an 8ft driveway. Neighbours house is unextended(bar conservatory) and original houses match up across the original rear walls.

We now want to create an extra bedroom for the kids. At the same time we've decided it would be useful to create a utility downstairs. What we want to do is put a 5ft side extension on at ground floor level, this would run along driveway and contain a utility and also allow us to extend downstairs toilet to be a shower room. Technically I think we could complete this under PD as that part is single storey, though it does extend past end of original house it would match to the existing extension.

My main query is upstairs. Again I believe we could extend above the existing extension across about 2/3 of the house(this takes us up to the window in the existing rear bedroom) so seems the best place to stop. Again we are staying away from boundaries if we do that. However the room size we'd get in the new bedroom wouldn't be much bigger than we have. As to get to this new room we're stealing part of the bathroom the plan is to extend out sideways 3ft over the new ground floor extension. The bathroom would therefore gain 3ft, and this structure would still be 'behind' the original rear wall, what my main query is, is whether we can continue this 3ft extension on the side of the rear extension. This is where I think we start encroaching on to the neighbour and his right to light stuff. By my calculations the 3ft side extension at that level would still allow 45degrees from the midpoint of his upper window. I also think that we could have this extra 3ft with a pitched roof i.e. a continuation of the main roof

(to steal someones thunder basically the side will look like the east elevation of here http://planning.bournemouth.gov.uk/OnlineRegister/Attachments/76535/Elevations_201032211587.pdf )

My concern is that because that last little bit of the second storey(over existing extension) sticks out that extra 3ft. The rest of the plans I think don't have much that could be objected to within the 'law' and also based on similar schemes nearby.
 
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Just done some further sketching and reading up on this. By my calculations if the rule is from the midpoint of the nearest affected window we should be well within the limit if it's 45 degrees that is allowed. Reading some sites suggests that occasionally 60 degrees is the rule for upper windows, or alternatively the corner of window nearest edge of property which both would mean we lose a chunk off the corner of the upper extension.

Has anyone any real experience of councils and how they enforce the rule? If it makes any difference both houses are facing NNW from the rear face so the amount of sunlight lost I assume will be negligible anyway regardless of any structure we put in. One neighbour has completed the extension over the lower one but not extended out those few feet like we plan to so there is no exact precedent. Just want to have something decent in my head before I speak to any planning dept and put my foot in it and turn them against the extension through my questions
 
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There are many members on here well versed with approaching Planning Departments, frankly though (please don't get offended BTW) your post is a bit too long winded/confusing which may be why you've had little response. Please repost with a simplified version of the text and a simple sketch showing the existing and proposed ground and first floor plans with rudimentary dimensions which will make it a lot easier for us to answer and get the ball rolling. ;)
 
No worries, cheers for that. I have attempted to do some drawings so once I scan them will try and add them. As we were trying to work out what to do I hadn't really drawn anything up so far hence the overly verbose original question.
 
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The red bit is where I'm not sure on the planning as it's past the existting house lines and also more over towards neighbour

(of course neighbours conservatory shoud be on existing ground plan)
 

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