We are all different, and we all have varied resources. I've had 4 telescopes in my life, and I've had them 10, 9, 15 & 11 (so far) years respectively. Each one has been a significant upgrade when either the old one has broke, or become too frustrating to use. Getting the most out of the current telescope I have is about tweaking and expanding it over the years. It involves spending relatively small amounts of money compared to the initial cost, but it often isn't money I can spend without some thought. Hence the discussion here.
I would agree that monetary philosophy is not a subject for discussion. There does come a time when tweaking a telescope brings little or no satisfaction, but only the particular individual knows when they've reached that point. We cannot decide that for others, or indeed judge others if they decide to get a better telescope when we think they could have got more out of the one they already had.
Personally I feel that I've a long way to go yet before I need to contemplate a new telescope. There will come a time though . . .

I use an 11" reflector (Celestron CPC 1100) and a 3" refractor, (Sky-Watcher ST80) mounted on an equatorial wedge, housed in a 2.2m Pulsar observatory. I use a ZWO ASI 120MM, ZWO ASI1600MC and Canon 1300D for imaging.