Looking at the lines on your house (where it's not finished out, needs to be backfilled), you're going to need some retaining walls. I'm not sure why this wasn't addressed during construction. Poured concrete retaining walls could have been done at the same time your basement walls were poured. imo, since your GC (if you have one) didn't figure it out during the build, you should contact a landscape architect/designer who can help the house blend into the land. Congrats on getting power. Hope you enjoy your new home.

I must be misunderstanding... You said (or so I understood) that you don't want to tear down the laminate. However, then I read that you are leaning toward putting the Wilsonart the exact same way as the current laminate. So ... I'm not sure how to help you. Please clarify for my aging brain and I'd be delighted to help.

We lived in a 100+ yr old house with plaster walls. We always hung the rods from the wood trim on the Windows. We didn't have a problem hanging pictures or heavy mirrors. We usually just used large picture hangers, the kind with the nail already in them that go in at a slant. If you try to drill a screw straight into the wall I don't think you will get a good solid hold because the screw will go completely through the plaster and wood lath used to hold the plaster on it. You may be hitting a nail in the lath which is why the bit broke.. I would, go to the local hardware store and ask them what to use to hang curtain brackets on a plaster wall. They should be able to help, surely there is a fix for it.

If it were me, I would go low impact. You're not crazy. The charm of an old house is that it doesn't look like a new house. You just have to make your own call as to where the line is between "old house charm" and jankiness. A good floor guy can do magic to patch a floor. We have a large patched area which is invisible in our kitchen. Can you buy reclaimed flooring to match what you have from anywhere locally to use for patching, or can you salvage any flooring from any of the other work you're doing on the house? You might need to do some legwork but in most areas with a lot of old homes, there is someone. Another note...you absolutely do not need to tear out the old plaster to rewire if that is a concern. We just had our entire 1914 bungalow rewired, and in many places brought up to code, as part of a larger project. Basically the only holes to patch are where the old outlets and switches used to be, if we are not reusing them. They dropped in the new wires and left the old ones disconnected but still inside the walls. There are other reasons you might want to open up the walls, like if you want to add insulation inside the wall cavities (because of the need to install a vapor barrier, not bc of the wires), but a good electrician would not suggest it just for wiring. The vast majority of the plastering we had done was from reconfiguring the floor plan and moving our upstairs ceiling up 7". You can see the latter below. The texture of our old horsehair plaster (rough surface) does not quite match the new, but we don't expect that to be an issue once it's prepped and painted. I'm sure the availability and cost of doing blueboard and plaster varies by location, but here in Boston it is fairly standard.