Waht a mess but I think short of going back to a flat roof which IMO would be my first choice the above ideas can work but I bet they will not be cheap and so you will need to decide what style you want 80s contemporary or MCM two very different styles . IMO with your interior that I see I would go back to tflat roof and embrace the MCM In case you haven’t figured it out I love the simplicity of MCM design

Where i this house? I would worry about snow/ice sitting in any flat roof or dead end of the pitch

I am unclear if your main interest is aesthetics or needing reconstruction for interior livability. But you need a real architec!

For a quick fix to the front of the house I would look to make the tops of the central 4 tall windows slanted, even if it meant simply applying obtuse triangles of wood to get the effect, I don’t know why the area in front of the house is so orange, but I would change that. It is hard to see your front door but the area I can see might look great with a dramatic painted wood relief of oversized, overlapping primary geometric shapes: a square, a circle, a triangle. A constructivist desgn.

on the left side of the house it would be fun to plant a long and dense straight line of bamboo, but prune it every year so that the heights of the trees formed a sharp descending line, with the tallest tree at the far left, and the shortest closer to the entry

I agree with Patricia that a flat roof is what this home is screaming for. If I were to do anything, and I would need a 3D rendition to know how it would work out on this home is a raised clerestory roof over the center main space of the home.

Here is a street view of my parents home that had a multilevel flat roof (the lower portion over the LR is not visible here). The visible raised area is over the kitchen and our kitchen was always bathed in natural sunlight even though it was in the center of the home.

I found these photos from a renovation where they restored the same type of secondary raised flat roof.

Outside

Inside

You would not get useful attic space, but that is not much of a loss. I have a crawlspace attic in my current home with a low slung roof and have only accessed it for electrical work. Had one in my last home as well - tried storing a few things up there, but if it was used seldom enough to make storage in that space a reasonable option, I didn't use it often enough to keep it. The only thing I kept up there was a few boxes of Christmas ornaments. The tree and larger boxes or heavy boxes were too awkward to get up there, so they got stored in the garage.

Am I the only person scratching their head trying to figure out how the current rooflines drain without causing water damage? Or is this house in a place where it does not rain or snow enough to matter?

Thanks everyone for the input. This is in Florida so no risk of snow build up but rain is definitely a concern and there is wood rot to address. On the tall raised sides of the roof pieces they made a slight bow out similar to a cricket to help steer the water away but it isn‘t ideal. We do want to embrace the mid century feel and were trying to see if there would be some way to accomplish that without ripping off the entire roof. The atrium on the back limits options as well. If we went back with more flat it would still have a slight pitch rather than truly flat.

Interior space is good as is but if we changed roofline we considered adding some vault to the living. I agree @User the orange (more red in person) painted concrete has to go. Will repaint or put tile etc. @Jennifer Hogan thanks for sharing those pics and input about attic space. We are leaving a house that had walk out attics so it will definitely require minimizing “stuff”! Not a bad thing though!

Since the house is in Florida, will a new roof have to meet current hurricane standards? If so, it'd be best to find out exactly what those are before spending a lot of time (and money) on designs that you will not be allowed to build.

Designs like Jennifer Hogan shows were popular with architect-designed custom houses in my area in the 1960's and 1970's. The clerestory windows were brilliant.

The flat roofs also are usually done in rubber and they last forever. One of my friends installs rubber roofs and loves it because he never has to go back - it is once and done for the next 50 years.

It also comes in white which is excellent for Florida where you want heat reflected.