What are your thoughts about moving up product line(s) within a Company?

I am lucky to have a best friend that sells and installs audiophile and videophile systems for happily wealthy.  That has allowed me to not only listen to some of the finest equipment out there, but also buy some amazing lightly used items,  I went through (up the line) some amazing Dahlquist speakers long ago. various Mac Pre Amps, Nak Decks, and buying Amps that were 'blessed' by Nelson Pass. So I am a Pass PreA and Amp guy.  I have been up the line with B&W speakers till my 802 D's and stopped. I have done the same with Bel Canto DACs till the 3.75 and stopped ( although the new Black intrigues the heck out of me ) ( Love my Wadia 521 DAC too ) .  I'm a Kimber Kable guy and have gone up the line with them too and never a bad result from Coax,to IC's to 8TC bi-wired speaker cables.. .  If anything I am loyal to certain brands and engineers because I have never been disappointed in their products or their service.  Live the dream and trust your favorites ( until they sell out to someone else ala Classe' , etc.  ) 

I like co.s that have been in business a long time and have good customer support.

e.g. Magneplanar, Vandersteen, Bryston, Audio Research and many others

I've had very nice components where the small, innovative co. was wiped out and then had trouble getting them repaired.

A vision pursued over decades, honing the SQ every several years counts too (see above)

I have moved up the line with Thiel loudspeakers starting with the SCS 4, then 1.7, then 2.7 speakers. I could definitely hear good improvements everytime I moved up the line. The more expensive speaker always had sweeter and more refined highs, as well as punchier and more extended bottom end. 

If I could afford too I would. but I cant so I dont. So there!

Once I find a company where I love their philosophical approach, reliability, customer service, and most importantly "signature sound" meaning what they value most in reproduction - then I am inclined to up the chain for me that has been loudspeakers Von Schweikert, amps Nuforce/NuPrime and source Ayon