Do sound characteristics matter when moving from midfi to hifi?

Like many, i'm waiting and researching while waiting until I can afford my next upgrades. As I read the pluses/minuses of each piece, I wonder if it only matters once you reach a certain level. Hypothetically, if going from Sony, Marantz, Schiit am I going to find something that I don't like about Pass Labs, Conrad Johnson, Coda? Everything I have, I bought online so I din't audition anything prior. Back in the 80s, when I bought my 1st system, (Yamaha, Infiniti) I bought what I could afford again without much auditioning. Just curious on the point of view from the more seasoned crowd.