Not enough information, not really an internet question. You need a local contractor to look at it.

The red is where the supports are.

The green is what I want to remove.

The yellow is the current vaulted living room.

The purple is the kitchen I want to vault.

The orange is the rest of the house that will be left with a normal ceiling.

I agree, especially since the home is built into a hill, you should talk to a GC who is familiar with houses built like this one. No doubt your land is gorgeous!

Thanks, @cupofkindnessgw. I plan on landscaping everything after I finish the renovations. I have these stumps that won't stop growing trees!

Save 20K and stick with the flat ceiling. Vaulted ceilings in kitchen just cause design problems because you need a full custom maker to take advantage of any angles. Standard cabinets are rectangles, and rectangles do not fit into triangles without having awkward space left over.

I am actually going to move the kitchen into the living room, so that would be the dining room. If I was to vault it, I would do it myself. I definitely wouldn't pay someone to do it because of the outrageous charges it would incur. That is a good thought about the design, though. My goal with this house is to do 99% of the work myself.

If it is a truss constructed roof you are going to need an engineer to sign off before you start hacking up the trusses.