If you've got someone locally to guide you, then buy the best gear you can afford and go from there. Otherwise, if you're learning 100% on your own, I'd suggest the crawl/walk/run approach. Start with a single stage press so you can learn all of the ins and out of changing out dies properly. Use a beam scale and hand trickling to get the finer points of powder charges down. I promise you: as your skills and knowledge evolves, you'll have a better understanding of what gear will improve your loads. Learn how to play on a cheap Sears guitar and then when you're finally comfortable, move up to that Fender Stratocaster.
While I agree with your idea of starting with simple, uncomplicated, easy-to-use reloading equipment, and learning the basics, I must disagree with your guitar analogy...
Starting off learning to play on a very cheap guitar, with possibly wrong strings, crappy quality, out of adjustment action, etc... may just put a guy off wanting to learn to play guitar! Apples to oranges here... but spending good money on a shitty guitar is just wrong advice, in my opinion. There are lots of decent guitars available for a beginner...
So now, with reloading equipment, your cheap guitar idea might be expressed by saying, "buy a Lee turret press", as some consider Lee reloading equipment to be low quality. I've used it for years. I would call it the Sears Craftsman quality of turret press. Usable. Serviceable. Low priced. I used Craftsman tools for years as an A&P aviation mechanic and while they are not Snap-On, they work. I would recommend Lee reloading products the same way.
However... I do absolutely agree with buy the best you can afford, whether a guitar, mechanic's tools, or reloading stuff. Expensive is not ALWAYS better. Just higher priced.
I apologize if I seem to be contrary or whatever; I just like reasonably priced, usable items.
And while I'm at it, I will add what I think are the basic reloading items needed to get started:
-brass, for all calibers you want to reload. For bulk ammo, like .223/5.56/.45acp etc. I like picking up range brass. People who use public ranges often leave their brass. It's like leaving money laying on the ground. Pistol brass has never been an issue using 1x fired.
-primers/powder are in demand and will be the most difficult to buy. Buy in bulk whenever you find it. It won't be there by end of day, so buy what you can afford... today's ass-rape prices may look like a bargain next year or two years from now...
-bullets are still available. Buy in bulk (with the caveat that you have to find the right bullet/brass/primer/powder combo recipe that your gun likes... Then buy in bulk. Starting out, we all have to experiment with hand load recipes, but some common loads are "tried & true".
-brass tumbler & media
-brass trimmer. May not need this until you start reloading a piece of brass multiple times.
-good press. I like a turret press where you can mount multiple dies and not have to remove/adjust/reinstall multiple dies for every different step, every different caliber. This is why I recommend the Lee turret press. One die disc holds 4 dies. Easy-peasy quick-change discs allow you to switch calibers instantly.
-good dies for each caliber, (primer punch/full length re-size die, bullet seating die, crimping die).
-good quality, comfortable to use primer seater. I really like the Co-ax. I hate the Lee hand primer.
-powder measure. For pistol, I determined what charge of my favorite powder I wanted, then made a simple scoop from an old .45 case. For rifle cartridges, I like the Lee accurate powder thrower. Then I got a RCBS Chargemaster Lite and wondered how I ever lived without it. It's slow, but fun to use.
-beam type powder weight scale. Again, Lee.
-good little funnel for charging cases.
I'm sure I've left something out.
Former USArmy 67T/67U/contractor. Chinooks are the Cadillac of US Army helicopters, but I loved the Huey most.
Edit to add:
-reloading books/manuals are ABSOLUTELY ESSENTIAL.
And again, while I'm at it... You can have a great deal of fun and save money using cast lead boolits, especially with bulk pistol loads, like .45acp. A lead melting/casting pot, and a good supply of lead are pretty easy to find. Soft lead is OK for a lot of stuff, like pistol cartridges, but higher pressure cartridges need harder lead. I need more education in this area, but I found a great deal on bulk cast lead .45acp boolits.
So... if you can go dig out all the lead from the local berm, you might consider recovering the lead & copper for re-use... Just an idea.
