Rebuilding: should you extend yourself further into negative equity?

Negative equity conundrum: when you've already lost so much money on your home, is it worth shelling out to improve it given you'll be stuck there for a lot longer than anticipated?

Our house was built in the 1860s. It's the bit that was built in the latter half of the twentieth century that's the problem. A large, flat-roofed lean-to houses our kitchen (complete with badly installed veneer units, sudden changes in floor level, no insulation or ventilation and floor-to-ceiling 'harvest'-style tiles) and bathroom (the walls are covered in a shiny black lino-like material that we are too afraid to rip off lest it takes the walls with them).

SLIDING DOORS: Wouldn't it be lovely to swap extensions and live in this one (above and below) in Foxrock by Moda Architects? I also covet the print of Sanna Annukka's Spirits of the North, which is hanging on the back wall of the kitchen. Photos via OnlineTradesmen.ie

Something needs to be done about the extension, as the roof is not going to withstand the elements for more than a few years. Then you're in a position where you must ask, should we just do the bare minimum (i.e. re-roofing a terrible extension) and do nothing to improve the value of the house or make structural changes that will increase its size and function, making it possible to live there in comfort for however long it might take to be in a financial position where we can move on?

HOUSE ABOUT IT? The rear of our home as it is now after Eoghan painted it white. This was a big improvement.  I'd love to knock down the extension and replace it with a two-storey number, complete with sliding doors. I'd like the original stone wall to the right to inspire any future work.

And if you're considering structural work, should you simply rebuild the existing ground-floor extension and leave the kitchen and bathroom at their present size, or go the whole hog and make it into a two-storey extension (as many of our neighbours have already done), changing your house from two-bed to three-bed and putting the bathroom upstairs? (These conundrums pre-suppose that the funding is available!)

The first thing we did upon purchase in 2008 was to dig out and terrace the back garden (our house sits on a slope), the level of which was about four foot off the ground. This was a huge job as we have no side or rear access that could bring a digger onto site, so the building team had to resort to the old-fashioned spades and wheelbarrow approach. Will post up a 'before and after' come spring when we've got the garden looking a bit tidier!

I confess that I already have one or two things bought for this extension, which are stored at my parents' house at present. Don't tell Eoghan!

Here's a selection of some fantastic extensions which I keep in my 'Maybe One Day' folder, aka Pinterest.

RAISE THE ROOF: This Dublin extension is by the talented Ailtireacht firm. The shadows created by the slats against the original rear wall are beautiful. I love the continuity of the bench inside and out. Image via Evdes

BEAM ME UP: I've had the pleasure of being inside this 1960s home in Knocklyon where young practice Carson and Crushell did a stunning retro-fit and new extension. It was open to the public as part of last year's Open House Dublin event. Image via Open House Dublin

PERFECT FROM A TO ZINC: I'm a huge fan of the zinc cladding of this Dun Laoghaire extension by Browne Architects. Photo: Browne Architects

STOREY-TIME: Flavio Lombardo Architects designed this striking extension in Sandymount. Image via Homedsgn, which has lots more photos