I'm not sure if I will have much to add that many here have already stated, but I will throw my .02 in.
I am not a huge IP grapher (I have done some shows, some stadium waiting when I was younger and some local signings). I generally don't care to bother guys when they are not intending to sign. Do I have to pay more for some of the autos I want? Yes, because otherwise they are free.
I am like most autograph collectors in that I started out all over the place and narrowed my collection down (for the most part) to autographed baseballs of Hall of Famers. Starting out, I got the guys at Twinsfest that I could get in person (Carew, Killebrew, Molitor). After that, I nabbed a couple guys in the mail that were fairly guaranteed (Nolan Ryan, Doerr). From that point on, I relied on Steiner, UDA, MLB holo, Tristar, Mounted Memories and a few select other instances for the most part. Again, I generally have to pay more for their sticker, but to me, spending an extra 10-50% (or whatever it breaks down to....depends on the player) is well worth having the extra piece of mind. Now, if it were to come out that Steiner has been selling fakes for years, then I would have a nice chunk of my HOF collection that would be considered fakes (although many come with MLB holo as well which is as rock solid as it gets). I, like you, have evolved fairly slowly being able to pick out the good from the bad and I am still learning. If we had a Mantle quiz on this board when I started, I would have gotten 3/10 just from dumb luck. Now, I think I would score in the 5/10 range or better, but it would be with reason.
If you are going to pass the reputable 1st party authenticators, then you are definitely going to have to struggle with your points you made. As far as the gurus on this board, I too would LOVE to know what they know when making opinions on just about everyone, but I understand their hesitation to spill their secrets whether it be to make a gain financially or to withhold their level of knowledge from the scum in the hobby.
At the end of the day, you work hard for your money, so just be happy with what you buy. If it hurts to spend $300 on a ball that you are worried about, don't buy it. At that point you can spend $500 and get one with a UDA hologram or you can just keep waiting for the right opportunity where you are more comfortable. You sometimes have to take stabs in this hobby too which can burn you, or pay off big time. I spent $100 (not huge money, but at the time it was a lot for me) on a Joe Mauer signed jersey off of craigslist thinking, "what a great deal, the jersey alone is worth more than that", only to find out shortly after that the jersey was a knock off and the Mauer autograph was crap. I also more recently purchased a 1927 Yankees baseball for $1,000 and it ended up being legitimate. The point being is that sometimes the thrill of the chase and to find those diamonds in a rough is just as fun, if not more than adding the item to your collection.
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