New horizontal siding would be the best choice..........Hardie Board siding which is actually a cement fiber mix comes pre-finished in colors and is guaranteed to last for a long time (not sure how long)

The diagonal siding and the landscaping are the issues that date the house. Hardie is a good product. Maybe their site has a "try it on" section where you can get a feel for what looks best.

@Lisa M I hear you but when updating, one needs to also consider if there is any true architectural significance to what you are changing. Plus one needs to consider if the original was actually done well or was it just done to the trends of the time? Is preserving trends of the time of architectural value? Maybe. But we live in the real world with budgets, labor/material availability and new concerns impacting our decisions. Horizontal siding application requires expertise to avoid the risk of water leakage around windows, doors and other openings. Water finds its way and when it does it's damaging and can have adverse health impacts. Accommodating the horizontal cuts results in a lot more wasted material. So does today's enlightened awareness of sustainability and reducing waste secure a higher place on the priority list than preserving a look that recalls the trends of the 70's? Not sure if you are working with outside tradespeople on your shed, but finding quality craftspeople to do specialized work well is a lesson in patience, often literally years out, in my very active region. Specialized labor plus more material equals more cost. What are the family's other budget priorities? Does preserving a 70's trend outweigh saving for a child's education or your own retirement? To answer your question: "why would you buy a very specific 1980 house and try to use it as a springboard to faking the look of new build houses on your inspa lists." In the current real estate market, most folks buy a house based on location, cost and the ability to actually get your hands on a house in this crazy bidding market. The house style often has little to do with the purchase decision. May I point out that the OP has two, not four or five different siding styles on her home. Even FLW used two siding types on his own Oak Park house. If it's good enough for ole Frankie, I'll take it! Could he have bricked the entire house? Yes, so is that shake siding an arbitrary decoration? Who's to say what's an arbitrary decision on any structure? Some thought went into everything chosen. Not everything is precious on/in houses of their time. I just gutted a classic harvest gold bathroom. Should I have replaced it with the same since it is of the times of the house? No thank you. It had a good run and kuddos to the tile craftsperson who installed a shower pan that lasted 53 years. And BTW, thank ya Jesus for "James" Hardie. Had the company he established not pioneered fiber cement products, we'd have a lot more asbestos, rotting wood, black mold and ear piercing wood peckers waking us up at dawn. Big questions are interesting to ponder. Just not sure making assumptions about a poster on Houzz and the decisions they made is the place for it. Probably better to post your big questions as your own posts for comment. But...that's my opinion.

I would change the siding to horizontal (to echo the lines of your house - I think vertical just would not look right except a small area around the front door to set it off) When you re-side, look at adding a little bit wider framing around the door and windows. You will want to paint the trim, downspouts, gutters all the same color - black would look good, white will work also. Pick a bold color for your front door (storm door too) although black is good there also. For sure, take out all those shrubs. It looks like you could keep the stone walls, but perhaps add a smooth top, like large cement look pavers. Or if it is even possible, once all the other changes are made and then you don't think the stone looks right, add a cement paver facing to the front of the wall. Low growing, ground cover juniper or similar evergreens would look good behind the wall. What am I seeing at foundation level on the house? Are those windows?