Is it going to be a 5 car garage??? That can be a problem. Can you turn the garage?

This needs an architect because massing is going to be so very important. Otherwise your house could end up looking like a Jiffy Lube with a house attached to it.

Standing seam roofs have been around for years, and their benefit that they last so much longer than shingle roofs.

I have become fasinated with the vintage corrugated metal roofs like you see below. They used to be used on farm buildings but now have made their way into residential buildings.

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The house and its ski slope roofs are at least consistent. Raising the roof, tacking on a larger garage and adding bigger transom windows isn't necessarily so.

Tell a talented architect of your vision, absolute needs and budget and let them make sense of it.

Look up the permits for the original house at city hall. Perhaps the original architectural firm is still in business.

It is much less expensive to stick with the original style than to remake a house in the current year's "updated" style.

We are adding a 3 car garage with bonus room/bath above and are extending the front of the house out to gain an inside entry way and master walk in closet on the right side of the house.

Then you must already have plans you can share.

"We love any ideas for how to add on and update the roofline so that it looks cohesive."

The first idea you were given is the best Idea you will get.

A great 80’s Contemporary like that would lose more than 1/2 of its current value straight off if that style isn’t honored and it gets some awful hgtv remuddle. It is a FABULOUS design style, highly sought after, and is very livable. Don’t ruin it trying to make it something it isn’t. This is a 500K+ idea that needs an architect. Yesterday. And which will only return 1/4 of that expense if it is a split level. And might get you a 50% return if it isn’t.

As others are saying this is a pretty extensive addition and remodel. Would benefit you to hire an architect who can make the new house a nicely massed and cohesive whole.

What is your budget for a whole home re-imagining? Because you might be better off money wise doing a teardown and a whole new rebuild. HGTV has give people a fantasy that remodels of this scope are "just" a little work and money. They are NOT. Building a new house is easier most of the time, because you don't have to rebuild half the existing house to be able to add on another half house. The real world would dial that scope back drastically. Or move. Because you also don't want to be the biggest overbuilt house in the neighborhood.

The house is pretty great as is. The first commandment in home renovations is: First, do no harm. You clearly want a different house than you bought, and are proposing to harm. So, buy a different house. What you are proposing are like very very expensive couture clothes that do not at all fit the body underneath.

Sometimes the best way to update the look of a house is to buy a new sofa.

If you don't hire an architect, the chances you end up with something that will "stand the test of time" and "update the roofline so it looks cohesive" are quite small. You should also ask them about the cost of tearing down your existing house and building one you like better and look at the cost of moving to a house that better suits you, too.