Need a picture

I would say - add window boxes to the shorter windows with silk ivy and geraniums, plant the planter areas beneath with cottage plants - shrubs that flower / some evergreen, zig zag pattern, groups of same thing so they mass.

If you just paint out the downspouts they aren't so bad. Not sure you really need a new roof - they are expensive and you shouldn't do it until you absolutely have to.

Consider taking shutters off the large window altogether. It is lovely as it is - since the shutters aren't really wide enough to close over the windows there, it would be nice without. The door color is wonderful, but I wouldn't spread it to other shutters .. they are okay as is or darker brown / brown black.

The rest is just landscaping. You could do a row of flowering groundcover on each side of the long drive . the same one over and over is cottage charm.

Grow a vertical hedge shrub just outside the left columns of the carport to make a side "wall" - columnar plant that will be evergreen that your nurseryman recommends.

Plant a tree somewhere in the front yard and do a planting grouping with a pretty boulder and mulch in the same circle area. You might put a lodgepole or split rail or vinyl but same low profile - ranch fence 15' from the road and plant low shrubs (all the same - the kind that can kind of spill through like abelia grandiflora or mock orange) behind that so it adds to the ranch character.

Conversely, instead of spending fence money, just do a wind break with the plants - plant them at the points of rick rack / zig zag with the spacing between the points sideways at the recommended distance so they look fuller and visually fill in quicker. If you do a row across the front - hop the drive and get at least 3 x 5 in on that side too.

ps - consider moving before you spend $25k for a new roof .. that would go a long ways in a new home on things you could enjoy / take with you.