Have very similar car preferences as you. Over the last 20 years have driven only tahoes, mercedes sedans and toyota trucks.
Rather than getting a nice newer truck or car I went with older both.
I have a 2012 FJ Cruiser for pulling the boat, camping, beach, lake, taking the dogs, home depot and short trips. I do like the new land cruisers and broncos, and may get one after this dies. Has 144k miles and now that I have the other car am only putting 5k miles a year, so it should last for a while.
I have a 2018 e300 for longer trips. Yes maintenance can cost a lot, but compared to buying a newer one I could spend $3k in repairs for the next 10 years and still come out ahead of buying a new one. Mine has 82k miles and I got it for $17k, new ones are $50k. This is the 5th E I've had. They do start falling apart around 120k miles, but have had good experiences from 50-120k. I found a oil change place that lets you bring your oil and filter and does the change for $60, saving a few hundred over the dealer or nice shop. I'd do it myself but it's a huge pain to remove the skid plates.
There's something about Mercedes sedans that just seems better than any other car. I think @TwiceHorn described it as "design aesthetics" Everything just seems to be in the right place, seats are comfortable and better adjusting than any other, and it's great on the highway.