LESS is a one-sided word. It finishes 17 compounds in this list and heads none of them, so it can end a chain but never sit in the middle of one.
Each of these makes a compound ending in LESS.
The -LESS in POINTLESS is not the LESS in less money. It comes from Old English lēas, meaning free from or devoid of, and is a cousin of loose; the comparative less is a different word entirely. That is why it attaches to nouns and not to quantities — BLOODLESS, TIMELESS, WEIGHTLESS, WITLESS.
KEYSTONE is a free daily puzzle built entirely out of chains like these. You get the two ends and have to fill the two words in the middle. Three bridges a day, no account, no cookies.
Each of these has a page like this one. There is also an index of all 54.
AWAY · BACK · BALL · BED · BLACK · BOARD · BOOK · BOY · BREAK · CHECK · DAY · DOOR · DOWN · FALL · FATHER · FIRE · GROUND · GUN · HAND · HEAD · HOOD · HOUSE · LAND · LIFE · LIGHT · LINE · LOAD · MAN · MOTHER · NIGHT · OFF · OUT · OVER · PAY · POINT · POST · POWER · ROOM · RUN · SHIP · SIDE · SOME · STEP · SUN · TAKE · TIME · TURN · UNDER · WALK · WATER · WAY · WOOD · WORK