You see that a lot at the closest LBS to my house. Its a high end MTB outfit and while they are helpful if you are interested in their thing its the total opposite if an old guy rolls in on a 15 year old cargo bike. You can see the mechanics mood drop when the old guy says "I got this for $200 x years ago and it works great... now please help me adjust the gears". At which point the spiel on buying a flashy new bike comes out and you can see the look of incomprehension on the old mans face. He can't even fathom why anyone would want to spend $300 on a bike let alone $2000.
At the opposite end of the spectrum is this old guy who works out of one room in a ratty old buildings. He fixes old bikes and stocks a few average ones. He was totally floored when I wanted to get a whole new carrier and baby seat at the grand price of $50. He'd rather work around the problem with whatever parts he has in his (large and well stocked) bins. He looked at my old (semi retired) cheap MTB with its low spec shimano indexed 21 speeds and said "Hmm.. expensive bike." Whereas the guy at the first shop said "Why would you even ride that?"
Different people have different takes on the game.

Personally I like the middle of the road, most of the benefits of the expensive bikes, but way more reliable than the cheap ones. Still, it is fun when I'm out on that old heavy beast with 25kg of kid on the back and I pass one of the guys on really expensive bikes looking most serious.