I'm hopeful that a pro will provide you with some great ideas. Yours looks like some of the "befores" that they do brilliant changes to on the TV reno shows. Most architects will come up with excellent solutions within the space if that's what's required, but nothing worthwhile is likely to be done cheaply though.

oops with the diagrams.. Note that the "shed like" part of the extension joins onto what must have been the original lean to that extends all along the original villa part. Note the pillar in the living area, that is structural. Another strange aspect is that the toilet juts out into the open plan space ( I think that could be remedied with $$s and it could fit into the main part of the family bathroom by taking out the old corner spa and putting in a smaller freestanding bath for example) . By the way, the "retreat" is actually a courtyard that could be a nice feature if properly landscaped etc. A new roof (to get a new roof line) might work on the shed like part, but the walls around the west and southern perimeters of the space are just windows/doors so I don't think they could support the weight of a "proper" roof rather than glass? Can you see that plan well enough and what info do you still need OkLouise (and others)? Thanks again for any ideas :)

Hi Sarah, hope you enjoyed your travels last night, that's something we have spent our lives doing plus living in different countries. Do look into the attic room/s they are lovely and the Velux skylights very unobtrusive, look great and if positioned correctly take care of venting any hot air, as I mentioned ours were pivoting ones and could be locked open in several positions. I much prefer these to dormer windows, you don't really notice them. The stairs were built off site and lifted into position and installed, built in. At the time we did ours a very good friend a builder did the same but just completely opened the whole ceiling space right out towards the gutters into a large bedroom play study area for his daughters, also using Velux windows. Glass ceilings, like Velux windows have been around for years, believe me I know, we're both getting older. Velux windows can be used as glass ceilings in opening and non opening configurations. I would love to see you keep the outdoor loo as well and updating the old shed into a new connecting space to the house, perhaps a glass breezeway. I will have another look at your plan again over the weekend. I love your front iron gate as well, auto sliding driveway gates work really well and would really fit with your carport. My brother in law put in a tall timber sliding gate at his last home, lovely cheers

Hi RePete, another app for drafting is Home Sweet Home which is free. My experience has been that some of the really good architects are happy to share their ideas when they visit as they enjoy the creative process so much. Eg Williams Burton met with us years ago (we are still figuring out what to do!) - and I was very impressed. We didn't use them as they are very fastidious so their builds take a long time and we can't cope with that but they do some amazing work on character homes in particular and although people think of them as only doing very expensive jobs, I am aware that they have also done some cheaper jobs where the project has got their interest. You could try talking to them and a few others from that "tier". I can't remember if we paid for the initial meeting, but if we did it was only a very small amount. I would seek as many views as possible (including here), keep trawling the net and pinterest as well as Houzz, look at lots of magazines etc, go to every open home that is vaguely like your style and ask the real estate agent who designed/built it... (hmmmm this is why we haven't started building yet after 8 years...) As Ok says, probably the only person that can determine what accommodation is required is you, so make that thought process a parallel one to looking at pictures. Good luck.