Half of your scope purchases were mistakes! You must be a hobbyist because hobbyists do those kinds of things.
Well, yes at least definitely the Owon.
The other scopes were not. To be honest: many years ago I was not ready to spend a few thousand bucks for a scope. My demands grew with my projects and as I am making money with these projects I was able to purchase better scopes which fulfil my needs better for more sophisticated projects.
As I always purchased with a discount and sold the equipment later often with profit, I could easily afford that approach. In fact any scope I purchased was purchased at least 15% below street price. I am sure I can sell my Keysight MSOX3024a any day and I will receive at least what I paid for - probably even more. So I used it literally "for free" for the last 30 month.
Thus my measurement equipment was growing with my requirements - and I frequently had newer technology at my hand - for almost no cost.
(btw: thats the positive by selecting measurement devices from respected brands: they do have a low loss of value over the time)In retrospect: would I prefer the other alternative?
Purchasing a scope years ago which probably fulfil my needs for the next 10 years? No! That will be expensive and in reality I would start looking for new stuff after a few years anyway because something will be missing.
As I said: as I work for a living, this approach (at least for me) was the better way: I purchase what I need now and tomorrow and sell it if it does not fulfil my needs anymore to get newer and better stuff.
Note: the above applies to business related stuff. For consumer stuff for private usage this is much different. So you better purchase the best amplifier and/or speaker or camera etc. you can afford. Because then you enjoy right from the beginning. It just don't make sense to buy e.g. crappy speakers and buy new less-crappy speakers a few years later until you then end with good speakers after 20 years: you just lost 20 years with crappy stuff, paid much more at the end and you will regret you did not took the good stuff right from the beginning.
Edit: because I really was curious and wanted to know, I added up all my scope purchases and sellings (including all costs such as shipping and Ebay fees) from 2007. I did not count in the analog scope I already had before and also not the current Keysight. Result: I made 328 Euro profit between 2007 and 2015. Thus, a frequent update of some gear might even earn you money if you carefully select.