Depending on the design, headless can feel a little different. I was a relatively new bassist when I played my first headless bass (Steinberger Spirit XT2). It took me a week or so before my hand stopped shooting off the neck when going for the first fret. Some (like the Ibanez pictured above) have enough "headstock" there that it should still feel like you have one. Others do not provide as much neck feel near the first fret. This may or may not be important, but is worth calling out as I could see it bothering some players.
). I believe he is an advocate for headless basses as well.