Aside from a negative equity situation, has anyone regretted moving up the property ladder?

[Treeeaj]

I’m so tempted to stay in my small terrace but have the chance to move somewhere twice the size and twice the price. I’ve been in my current place 6 years and it’s all very comfortable financially but very small. I’ve been gifted money to move so finances won’t change as such if I do it. I’m just stupidly attached to my little home!!

I haven't regretted it myself.

That is even with my first property being caught up in the massive price drop in the 90s. The amount I "lost" on my first property if you looked at it in isolation was horrific but of course the bigger property I was buying, had also dropped a similar %, so, as it was a more expensive property, then the cost of the bigger property had fallen more - so a good time to move, for me.

Of course, every situation is different.

I can't see how you could regret moving to a better property when you aren't stretching yourself.
Of course 'more expensive' or 'better' doesn't necessarily mean that much bigger. It might mean moving to a semi, or even a detached. Or it might mean gaining parking / a drive or a garage. Or a garden, or better garden. Or a nicer area.
Great to have a higher value property when it comes to a time when you want to downsize or move to a comfortable retirement village or whatever.

In your situation it depends if the money the new house would cost (and the associated longer term running costs) would give you more pleasure if you used it in other ways - eg bought a camper van/boat/horse, lots more holidays, retired from work earlier or cut down your hours, gave the money to other family members to help them out etc etc.

I've only moved up one rung of the ladder, from a flat to a house and personally I'd love more space at home, but it's ok not to move on if you love your home, the grass isn't always greener!