Short list, because everything that stayed had to earn its place in a bag I carry down two flights of stairs.
A six inch reflector on a manual mount. Big enough to show structure, light enough that I actually take it out on a weeknight. The heavier tube I tried first went out four times in a year.
Three, not a drawer full. Low power for finding, medium for most of the night, high power for planets and doubles when the air allows. A wide field eyepiece did more for my enjoyment than any aperture upgrade would have.
A red torch that dims properly, a Cheshire for collimation, a folding chair and a thermos. Sitting down is the single cheapest upgrade available: standing at an eyepiece, nobody holds still enough to see fine detail.
Nothing here is a recommendation, just what survived.