Quick System Building Pop Quiz:

I’m selling the old gear to offset the cost of the gear I just bought

Why not upgrade or spend the money on the main system. Instead of selling the used gear start a new system. This is literally how I was able to have a second system. As long as you want or need a second system. That being said I have only been listening to my main system. 

#1 for sure,

I have only 1 satisfactory listening room, and have an adequate system in my office. I want the best system I can afford in the main room. I just added a pair of Clayton Shaw Caladans, CODA S5.5 amp, and am having Aric Kimball build a Motherlode XL preamp……then will sell off my old gear.

It depends. If the system is very good, I’d definitely pursue optimizing it. It’s a great way to make subtle personalized changes to suit your tastes and room. I chose that path 30 years ago with what I thought was a really nice sounding system, and have refined it since....isolation, wires, bi-amping, power supply upgrades, mods, tube rolling, etc. Nirvana on a budget!

Starting from scratch can cost a lot of money, and is a shot in the dark whether or not it’ll get you any closer to where you want to go.....it’s so subjective and room dependent.

Number 2 since I'm still trying to decide what "good sound" is.

The first 80% is a lot cheaper than when going for the last 20%. Meaning before I go for the last 20%, I better have the basics right.

@mapman 

You are correct… I seemed to have a couple other systems. They have never been extra systems, but for a special location.
 

I have a system in my office. It started with cheap PC speakers twenty years ago. I used to work a lot. Typically a couple hours or more a night. So, I upgraded one piece every once in a while… until it was pretty good.

I started a headphone system at work twenty years ago. Same kind of thing. It was in between upgrades of my main system. Well, I am an audiophile… so, slowly over the years I upgraded it. 
 

For most of my five decades I never had a second system of any kind. But I would not create another sit down system for the purpose of normal dedicated listening.

@jond the good news is in cases like yours there are lots of very fine and affordable options out there to explore with headphones, earbuds, portable DACs and amps, etc. 

For me it's 1 simply because I only have the space for 1 system. I'd love to have a 2nd system to tinker with. I own two streamers, two Dacs and two amps at the moment so I am most of the way there but no place to put it!

I’d go for option 2.  I’m happy with my main system right now and I’d love to try some different gear.  I’d really like to try tubes and some horn loaded speakers or some other high efficiency speaker.

For a few decades focus was on improving main system, though did play with  fun vintage systems (when vintage gear was quite reasonably priced). A surgery made clear I needed a better bedroom system and remote operation.  Since then, I have had a great time mixing up secondary system combinations and new types of gear.

@ghdprentice , thanks for your response.

I do notice you list multiple systems? Is it correct to speculate that one system alone, no matter how good, can do it all for you?

Personally, that is how I tend to think about it. I have many different ways of listening via multiple systems, different rooms, different headphones, etc., each very enjoyable in unique ways and with different levels of financial investment, that makes it more challenging to state definitively which is the "best", and I also find I learn a lot that helps me with all when I do not put all my eggs in a single basket, per-se.

For me 1).

I always strive for the very highest level of performance possible at my income level. Dilution by putting money in duplicate equipment is antithetical to that.