Agree reroof
Not sure what is going on in front of the house. Fixing that up and landscape. Whatever colour for gutters tie it into the structures at front

I can picture a light colour gutter to break up the brick and roof colours. Maybe look at Colorbond surfmist looks like it would match the pergola structure otherwise classic cream. These colours go with everything and I dont think they date as quickly as some other colours. I really think it will give it a fresh look.

The house is 'of a certain era' , and quite dark , so you can concentrate on that , but I think it is actually the section that lets it down . It looks like a charcoal fence over the left hand side , and the white pergoda , and they look okay , but that path and the straggly garden that is sort of a dome , and the crisscross wall or whatever on the right side all date it so much .

Do the halfround posts around the nicest garden in white to match the pergoda , do the gutters in a silver , dig up the path and dome garden , do way more modern plants and a new path , pull down the vine and trellis , and you are half way there , for maybe $1000 spent .

I always wonder with exterior questions, is the landscaping going to be done as well if it hasn't been included in the question, or is there an expectation that changing the facade of the house alone will achieve the desired transformation.

It's a fairly inoffensive facades despite being dated.  Personally I hate tiled roofs of that colour and if it was me I'd just colorbond it. But that's expensive and not everyone's taste.  
I would definitely focus on landscaping because if you had a great looking garden no one would even notice what your house looks like.

Without painting you can only camo parts and break it up. Use tall plants or a trellis. Use out door wall art . Plus fix the path, it looks like only half of a body can fit on that walkway.

I got a quote to clean and repaint and seal my tiled roof for 5k, dark grey would really refresh and modernise. Google the look.

Having been a roof plumber for over 20 years, repainting tiles is only a quickfix and will not last. Dont waste your money. The best solution is re-roof it with colorbond iron, and install anticon insukation blanket durectly under your tin. We have done hundreds of re-roofs like this and customers have always been excited with the finished look. Rather then paint your gutters, install new colorbond ones.
With your colour brick, gutters and roof look awesome with monument. Fantastic combination. If not sure, paint a section of your tile roof with a roller and stand back and see for yourself. Remember- everyones sense of colour is different. The cost of this no doubt will be much more. Then wait and do it when you can afford it. YOU WONT REGRET IT

I would do a raised monument coloured raised garden bed at the front to marry into the slope, where the current sloped garden is. I would use black mulch and some nice low maintenance grass plants. I would then make that walk way two pavers wide, with white stones and some dark grey monument pavers as a border running up to your house. Paint the roof to match with your raised garden bed and dark pavers. Match your gutter with your roof. If you have the budget I would render your bricks and make it white, if not think about painting the brick. Cut back those vine weeds that are growing on that fence to the right and paint it to match your brick, If you decide to paint it or render it. If not maybe paint the fence black to make it look more modern

Thanks everyone! The comments have been really helpful- nice to see the place though others’ eyes. Yes to sorting out the landscaping along with the facade, it’s all things we’ll have to do bit by bit as DIY time and budget allow.
Went with monument for the gutters, and we probably will paint the roof in the end- colorbond would look nice but that’s pretty far over our budget. The tiles were also recently repointed right before we moved in, and the roof is otherwise in good shape.
Also yes to changing the path and the scrubby jasmine vine on the car port. Need to plan though, because we might change around the carport/driveway so that two cars can park side by side, and we’d probably do the path then. Little by little.

If the roof doesn't need painting and you asked about roof colour and heat, what's the intention with painting the roof? Do you have insulation/sisalation?

Doing things step by step as you can will make gradual improvements... get your overall plan in place and work towards it. Personally i think the roof looks fine and wouldn't go to the expense of changing/painting. Yes, stylistically its of another era but as long as your scheme is consistent it will carry well.  Trying to modernise to what is current now could just be jarring, as macyjean observed.
A simple change that might have a big impact would be the path, it's yellow and the structure is browns. Work out if you need the path in that location and that straight. If it needs to be straight... change the color of the pavers to a color from the house. Or at a minumum darks, not yellows. It could be a more modern ofset stepped path. Ie a paver set at each footfall with a gap and low grass between the pavers, or you could curve around the rise and approach from the top of the rise to the verandah. 
Simply having all the verandah and patio uprights in the same color will improve its visual consistency, shifting it from a hodge podge look to more thought out.