What kind of photos would help? More than willing to take some for a little free advice!

I'll try to address all those items in order. First, pictures. I tried to take many so you could see all the roof lines/angles involved.

The current mudroom/breezeway was a DIY by the previous owners. I don't think it's insulated, as it gets frost in the inside in the winter. It's not heated or air-conditioned, either. In either scenario, that gets taken out.

We have no restrictions, as we live on an acreage outside city limits.

I tried making a current floor plan using a (free) web-based program. Here's what I could come up with:

We live in the rural Midwest. Budget is pretty flexible. We have no intention of ever moving from this location, so resale isn't a huge concern for us. I'm not sure on the joists in the garage, but I believe the foundation is sound, and it seems pretty well-built. Plumbing would be the biggest issue here, but if we put the bathroom on the side closest to the house, that might help keep costs down (?).

as a guess, i'd say removing the breezeway and building a new 2 story addition between house and garage would

1. be cheaper than trying to add above an existing garage and breezeway. thats what i've found to be my experience in 30 years of doing renovations on various houses. foundations are pricey but contractors (correctly) need to price renovations to include all sorts of misery they might encounter dealing with building over existing space. i wouldnt be certain your garage was built to support a second floor, even if it was just built last year.

and 2. look better.

I thought it would look better, too. I could add two gables (one in front, one in back) on the 2nd floor to keep it symmetrical. I don't want it to "look" like an addition. Thanks for your feedback on the garage, also!

The height of the garage, rather it’s lack of appropriate height to meet the home’s second floor height, and the likelihood that it’s joists are incompatible with the needed strength of habitable space, means that it would need to be virtually 100% rebuilt to work as living space. That is probably more expensive than planning an addition correctly from the beginning.

The addition needs a good architect who can integrate old and new. Midwest single floor master suite additions average 125K. I think yours is more challenging than average, and it’s two story. So maybe 150-180K for the two story box with a bathroom up top.

You’re moving a kitchen instead of just doing a like for like replacement where it exists, correct? Like for like remodels averages 63K. Moving it into new space, probably adds at least another 10K to the new construction, because it will need all new electtical and plumbing in the new space. That’s more expensive infrastructure than say a family room addition. Add in some contingency, and you’re easily at 250K for this project.

http://www.remodeling.hw.net/cost-vs-value/2018/east-north-central/

The kitchen would only increase slightly in size by moving the right side over about 3 feet. Other than that, I plan on using the same cabinetry, appliances, etc. and just re-configuring where the stove, sink, and refrigerator are located. Here's a rough idea of what I was thinking for kitchen:

Thanks for the input on cost - I'll admit, that seems high for this area, but I don't have near the experience working with remodeling as you!

Unless you are in a very high COLA, it's usually much less expensive just to sell your current house and move to one that suits your needs already. There are exceptions, of course, like California metro areas, for example, but in most places that still holds true.

You will never recover the cost. Find a new home, and sell this one.

You will not be able to reuse cabinets when redoing the layout. Nor should you even try. You will have the full costs of a kitchen redo.

Or you could just do a single story Master addition, downstairs, and leave the kitchen alone. That’s much preferred for aging in place.

Thank you all for the input! Moving is not an option - we live on a working family farm. I'll be sure to let everybody know what we decide...seemingly much farther down the road.