Simple -- theres too much brown , too much green , and a blue letterbox . So what is best / easiest to change ?

I wouldn't worry about the roof -- it'll cost too much for any real benefit .

I'd do around the terrace ( the front facing edge ) in white , and the railings in white , and even those 5 brown pillars in white ( yes , I know , I don't like painting bricks either , but I would ) . Gutters in charcoal . Fences in charcoal .

Then all you need to suss to finish is the garage door and letterbox . Me , I'd go bright red , but maybe a slivery blue would work , most yellows ? I'd keep away from the 80's apricot and brown , beige and brown , or even strong blues or greens -- they all are well out-of-date IMO . A couple of really nice , stained cedar or similar natural timber garage doors would look great , but expensive .

Thankyou Pottys99, I love how you can immediately see a big picture and attack it simply with colour. The budget can do the garage doors if I can overlook the roof...

When I got the trims on my house painted, the painter did the roller doors as well. Sounds like the inside needs a lot of work, so that's where I would spend most of my money. Outside really only needs the trims repainted and a new updated letterbox.

I’d replace the railing. It does not meet current building code and is dangerous for young kids as it is climbable. Whilst I normally like open railing I don’t like
Being able to see into the bottom of floors.

Thank you me me, You are correct, the interior IS a 'money pit'! Gloriously authentic, but... Cracked shower screen & rot to boot.

Keenly observed, Kate! One rail has already fallen off and the building inspector highlighted defects...

Wow this a crazy bathroom and will look so much better gutted.

In the photo it looks like it was taken from an elevated position. With the height and the rake of the roof how much of the Dutch gables can be seen at street level? The pizza hut roofs were a much steeper pitch so the Dutch gable was much more visible and more of a feature than in your home. I wouldn't spend big dollars on the roofing when there are so many more important things to do.
Dr Retro of Dr Retro House Calls and Dr Retro Virtual Visits

I think always start with the lowest hanging fruit... start with what is unsafe then if you are living in it while you renovate do the inside next, as it will bug you more. I think replacing the balustrade and installing new timber doors would give it a great lift. Rendering really changes things, but i think it's not always necessary so do the other stuff and see. I don't think the roof will matter so much when you update things. Don't forget to update the front garden, those little conifers really date the house and a contemporary garden, maybe with natives, would really add something too. I think the green garage doors need to be at least repainted if not replaced. choose a colour that makes them fade rather than stand out.

When your bother-in-law visits, I would put on a red checked shirt and serve him pizza 🤣🤣

Ok with that lovely view I would do a wire rope railing. Not glass as it requires to much cleaning. And change all green to a dark grey or woodland grey

And ditch all the sheer curtains so you can appreciate the view. Add venetians or shutters if needed for shade.

Apart from being a guy , that pic of the yellow glass and mission brown brick combo -- especially with the spiral staircase trifecta ) almost sends me into spasms haha ( not in a good way either ) . Have you thought of removing the window and putting in glass bricks on that wall ?

As far as changing the roof having no real benefit , I still stand by that . Adding another floor or raising the ceiling MAY have a benefit ( up to you to decide if the cost / council hassles / etc is worth it ) but changing the shape of the roof wouldn't IMO -- as Dr Retro says , a roof on a 2 storied house isn't really noticable .

Just keep it simple with white shutters on that window, I don't even mind the staircase, all the lace needs to go, is that the "Chantilly Lace" that Elvis sang about?

There's a single storey house in my area that from memory (which lets me down constantly) that has that roof and had a simple exterior make over, haven't seen the interior, sadly

What area is the house in, the downstairs ceiling height doesn't look too bad except for the RXJ. Any budget

Any shots of the position of the neigbours house on the left to ocean views

Thanks, yes I have seen that, so both houses are the same set back, love the retro house across the street too.