I am a pretty forgiving collector so far as grade, and it sounds like you are going a very similar direction to me. I started out collecting EVERYTHING. I decided I wanted on contemporaeous card of each Hall of Famer, so I worked on that for a while. I think when I got away from that was the inclusion of the negro leaguers. I love that era but the reality is that cards exist for most of them and many are very, very expensive. I picked up a load of T205 skins from Marc at a very affordable price and then started builiding that out in low grade. The way I have it displayed it is a fun set to look at. The main thing that did for me is to convince me that completing a T206 520 was doable.It took about 4 years and I started with 150 or so I had picked up along life's road, but I should have it done in the month. I plan to work on upgrading it the rest of my life. I traded a lot of my Sam Rice type HOFers to make substantial progress on my T206, especially when the economy was really tight (I own a good business, but at one point my partner and I decided to cut our salaries instead of letting people go). There is no right way to do it, but do it in such a way as you enjoy. My tip would be that although my personal last card has been the O'hara variation, I think the comer is the Dahlen/Brooklyn. I have considered trying to purchase a few of those strictly for investment. They don't come up much.
I don't think of it so much as taming the monster as befriending it. Along the way you will learn things...come to appreciate some of the artists, and make friends.
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