Your photos aren't showing. Take photographs of all four sides of each room as well as entryways. Find out which walls are load bearing because they have to stay, or supports have to show in open areas.

Do you have any photos in addition to layouts? You'll need structural designer to answer your questions.

IMO the first step is to find out which walls are loadbearing and what kind of budget you have for structual beams to replace walls if load bearing it is not just knocking down walls without understanding the purpose of some of those walls and how you can get what you want. Right now the furniture is the least important item Are you wanting a formal DR you have lots of space between the kitchen and the DR now so with good planning you could easily have a nice eating space but we need more info. Once you get a handle on budget and waht walls can be removed then you will need an actual KD not a cabinet sales person or your contractor but a KD. I like that you have a LR and FR but I would change their uses since I like a FP in the LR and the TV in the FR with no FP. Since what I can see there is no place for a TV except above the FP which is usually the worst place for TV.

I know that the walls are load bearing, and we have the budget to take them out. (This is a house we're considering buying, it's well under budget). I'm just trying to figure out if I can even get it to a layout I would like. Thanks!

If you’re ready to drop 150-300K right off the bat, then you should be working with a local architect. Not an Internet forum.

If you want to keep the FR as is, I think you're going to have to accept a smaller island. I like itsourcasa's suggestion to put a prep sink on the island, and put the clean-up zone on the short wall. I don't like the distance between the fridge and range, and that the corner of the island is in the prep path, but I don't see an alternative unless you change the windows.

I used the standard-depth fridge and made the counters on that run extra deep, for more counter space around the sink. The uppers could also be extra deep, and could include a MW beside the fridge.

Thanks

Spend $$$$ on an architect and contractor. Or buy a different house. That will be far cheaper in the end.