dman, thanks for your post. It made me think and appreciate the journey...my journey! I began my second journey after the kids left the comfortable confines of mom & dad's house and went on their own. The "before" kids group had decent equipment like a Luxman R117, Yamaha NS 1000 speakers, and an Akai Reel to Reel, to name a few. But when my wife said, "You owe it to yourself, Go for it", I started again.
My point to this is first and primary, is research. Read, ask questions and listen. Call the company headquarters of the equipment your interested in and ask questions. Then, before you buy anything, find the right, knowable dealers. We all know that once the journey begins, there will be a lot of upgrades. Having a dealer who participates in your journey with you and gives you reasonable "Trade Up" opportunities is tantamount! Allow me to give two shout outs to 2 of those dealers - Eric at Salon 1 Audio and Taylor at Gold Print Audio. They do it right!
Then I agree, Clean Power is a must. Including proper wiring, upgraded outlets and a power conditioner. All a must.
After that, enjoy the swapping, the trading up, the tube rolling, the cable changes and the new equipment. BUT, take the time to listen and enjoy each new tweak before you do another one. Discern if, and what, should be the next move so you don't have regrets.
I have no idea if I'm done on my journey. As we all know, can I get any better? Of course, you can always spend more money, but are you getting the increase in benefits, or are you just spending more money? Don't go on an equipment journey...partake in a listening appreciation journey. Listen to your collections whatever format they may be and appreciate the sound you've created. Enjoy a good bourbon and get lost for a few hours before life interrupts. Enjoy the journey but enjoy the music escape first and foremost!