I'll give the other side of the coin and how I'm good with starting with an entry level machine.
I bought an Ender 3 Pro about 6 months ago. I'm retired and was looking for something else to have some fun with. I looked at a few and kept coming back to the Ender.
So, does it have all the bells and whistles to start with? No... But it printed right out of the box without too much drama. By going with this printer, I didn't spend a lot of money up front. That wasn't real important, but the cheap side of me didn't want hundreds of dollars sitting in a closet if I didn't care for the hobby. So that was my goal and the machine fit nicely.
Since then, yep, done some upgrades. The first major was replacing the main board and that made it run quieter if nothing else. Then I swapped the control board out and that has a few more bells and whistles.
Yea, probably spent as much to upgrade (never checked) as buying a higher end machine to start... But I also learned a lot about the machine and how it works. Doing the upgrades meant spending some time working on the machine itself along with doing the research on what to upgrade and how to do it. Had to learn a bit about modifying the firmware too.
I'm never going to make a dime with this... Probably never going to take on a huge project like this one either... I'm just having fun. I feel that by taking the path I did, I learned a lot more than I would have if I'd bought the "better" machine. So for me, it's all good. IMHO, it's a good way to start and you can always move up to a bigger/better machine if you want AND keep the first one as a spare and to do things like print out a soap dish for the wife (did one last night LOL) and stuff like that.
Using a car analogy, you learned more from fixing that cheap car in the driveway then the new car with the warranty that goes to the dealer. Probably had more fun doing it too!
That's my two cents.
@KevinB also makes a lot of sense about buying a better piece too.. It's up to you and what you want to achieve and what path to take. If I was doing this to make money, it would have been the best I could afford with the best bang for the buck options so I didn't spend any unproductive time learning when I could be making money.