Okay, I didn't take time but to scan the replies, but didn't see that anyone mentioned screening in the covered porch on the left. It would be quite easy to do so using the ScreenTight system. Just frame above the bricks with two by fours then add the system linked below. We did this to our front porch and it's the best thing we ever did. Not only does it work great for humans, but our pets love having access to the "outside" world while still being kept safe from all that's outdoors. I also want to add my vote to NOT paint the brick, keep shutters and if your garage doors are in good working condition I'd check and see the arches are removable before buying a new garage door. There are faux techniques to change the look further too. Here is a link that might be useful: ScreenTight

@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.

Thank you, Laura, Patricia and Glo! I do agree painting the trim the same as the house to blend in will help bring it more transitional than traditional. Great point! Will definitely be replacing deck railing to metal and front doors to something that brings in light. I love the frosted suggestion to keep privacy. By saying I want to keep the brick, I just don't want to replace it. I am open to painting it, but maybe that is a bad idea? I like to concept of dark charcoal, but the light brick looks a bit jarring against this. Should I look towards a lighter, or white palette for the exterior if I keep the brick as-is? If going with a darker palette, do I paint/wash the brick to be less contrasting? Also, I am still stuck on where I could add some natural cedar siding accents to bring in some nautral color/texture. Would I do this on the right entry wall, the entire entry cove, 270°?

Love the all monochromatic paint scheme. The color to add to your mix to sample is black fox by Sherman Williams. That labor and materials price doesn’t sound that shocking to me I suspect you’ll spend a ton more ripping all that off and putting on hardy and repainting. That said I think Hardy is a good option for you but don’t expect savings