Do sound characteristics matter when moving from midfi to hifi?

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? 

I think if a guy has a $500 cd player and $1000 speakers, he will still appreciate the upgrade from a $500 Sony receiver to any of those amplifiers, yes. What you are not going to like with those amps is the mass. 

And then when funds permit upgrading source or transducers will be even more noticeable and appreciated with the quality amplification. 

I doubt you would find issues with higher end gear compared to Sony, etc but if you upgrade one piece at a time, a better piece of gear may make shortcomings in other parts of your system more noticeable.  

How much do want to spend when it's all said and done?  Are you planning to upgrade the entire system now, or one piece at a time? 

I would be upgrading one piece at a time. 3K-5K per. My question was more of a hypothetical. I can't imagine buying Mcintosh amp/preamp without audition and thinking this isn't an improvement over the current gear.

Hi, I grew up with with mid Fi in the 70’s. When I stopped I had a Sansui 9090 and JBL’s , Pioneer TT and a mediocre cassette deck. Years later I got the bug and did a mid Fi surround system , Yamaha , Klipsch, Oppo. About 10 years ago I wanted to get back into stereo. The first issue is the lack of audio shops. I’m near Fresno and the county population is over a million and we have a single Magnolia at Best Buy. So at first I went back to the stuff I left off with in the 70’s and early 80’s. I found out that gear didn’t sound as good as I remembered it. I tried to revisit the Dynaco stuff I had as a kid and was not satisfied. Given the lack of any ability to audition locally , I did a lot of internet browsing and took a few estimated guesses. I got back into tubes with a little Had Inspire amp, a Rogue RP-1 pre and Zu omens. I moved up in DAC’s to a Schiit Yiggy and a Innuos Mini streamer. Tube prices were still reasonable so I spent about $2500 rolling tubes. I’ve had a great time and a satisfactory learning curve. Today I’m moving up again with a pair of freshly serviced and modded Rogue M-180 Dark’s and a Rogue Hera pre. So once again I need speakers and there’s nowhere to go. I’ve received some great advise but to spend $5-10k on new/ used speakers leaves me in that position again. I’m finally to the point where I must go out and audition. So I guess it’s off to LA or some other big city. Looking back at my mistakes I should have attended audio shows and sought more advise on equipment compatibility and synergy. Also understanding how given speakers interact with my room and certain amps. I really miss the old days of walking into a store and auditioning multiple systems and getting experienced advise. But I always remember that it’s as much the destination as the journey. I wish you a happy experience and hope you meet some great people as I have. Regards , Mike B. 

one piece at a time and huge jumps? You won't hear much of a difference first