pp, that nice vinyl is ugly.

It's expensive but easy to do, and like PPs I would suggest the fiber-cement option as opposed to wood. One way to justify doing it would be to add rigid foam insulation as part of the process - might even be eligible for tax benefits or a utility grant depending on jurisdiction (not sure what the deal is around here, but in New England the local utility splits the cost 50/50 with the homeowner up to $50,000.)

That is what our vinyl siding looks like and I hate it. Replacing it was too$$$ for us though.

don't do it unless you are doing hardiplank. You can also get vinyl siding that looks 1000 times nicer that has more contour and shadow lines by picking beaded or lap.

NICEr vinyl siding:

I would not do wood - too much maintenance. But Hardiplank would look nice. It is $$$$$$$$$$.

We did it. It was $$$ and we had a tiny house. We did a full tear off, foam board, tyvek and hardiplank. Huge improvement. We replaced the window a few years ago before we did the siding.

Has anyone done this? We are looking at houses and I often see one that is a colonial with god awful vinyl siding and cheapo windows. The interior is livable. I had an idea that I could get someone to strip the vinyl and put hardiplank or wood. Also, of course, replace the windows in the front of the house to improve curb appeal.
Thoughts?