Overkill or just badass

My daily hauler is a very badass one ton diesel. But my son and I have been discussing the need and being time to step up our set up. Our current trailer is a 20' 10k two axle tilt bed with 12k winch, bumper pull. I am always looking at semi trucks and gooseneck haulers. I told my wife i was thinking about selling our old trailers and getting a new 24+4 or 28+4 gooseneck. But thought maybe should keep our bumper pull as its sometimes a tight spot to get into and is nice to have a smaller trailer if needed. She said just keep the old one too, you'll never get what you want for it trade in or selling it anyway.