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I know you asked for info from a seasoned reloader and I do not qualify for that. I can relate the experience of a total newbie, what I got, what it cost, and my satisfaction level.

-First, I only reload (and only plan to reload) one caliber, 30-06
-Second, I have only reloaded and shot one set of bullets. Definite newbie.
-Third, I do not have any pre-conceived bias towards any brand or type of press
-Fourth, I will probably not burn through more than 20-50 rounds per batch, one to two batches a month.

I purchased a single stage Lee Breech Lock Challenger kit. It was inexpensive, pretty much included everything (but the dies), and looked pretty easy with respect to changing dies. It functions well with the limited experience I've had thus far.

With shipping, dies, extra collets, length gauge, powder, primers, bullets, and crushed walnut shells ( using my kid's rock tumbler), I have approx $200 invested in everything. Since then I have spent another $20 for a bullet puller and plastic storage case for loaded bullets. My initial purchase was over the internet for the press kit. Since then I have found a killer re-loading store with good prices here in Houston and bought the dies, powder, etc. from there and will continue to do business with them vs. online from this point.

It is simple, I do everything in batches, only change dies once between batches, and hand prime.

I am anal about measuring, verifying, and re-verifying powder charges. Given this and my low volume I probably will never invest in a progressive. It is an enjoyable hobby and I am now hooked. Good luck in your research and hope you find a kit you're happy with!