I’m looking for some history lessons about 1st edition base set 
Mostly looking for stories that current sites (like the awesome pokemonprice for example) cannot tell because it’s too long ago.
For example, were PSA 9 1st edition holos from the base set ever considered cheap?Did people sell them off at prices like $30? Most like current WOTC sets nowadays, or maybe a few years ago already by now.
I do remember the PSA 9 holos having risen from like $300 to close to $500, but I haven’t been around before that time, but from time to time I read some incredible stories.
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Back when 1st edition base set holographics were $30 each grading was barely a thing in the pokemon scene
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I believe smpratte mentioned somewhere that a psa 9 1st edition charizard was once $250 region ! So it shows haha
You can look at eBay listings as far back as 2004 using PWCCs market price research tool www.pwccmarketplace.com/market-price-research
I believe you need an account to use it, but it’s free to make one. This is the best free way to look at historical data that I know of.
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I believe it was in one of his Q&A videos where he was asked if he had any regrets, or he was explaining every collector has regrets in hindsight… something like that.
And I believe the figure that was thrown around was $300,- (but I thought he mentioned he had sold multiple copies at that pricepoint, but not graded) somewhere around mid-2000, when Pokémon was at its all-time low and he came back to the hobby.
Take the above information with a grain of salt, my old brain isn’t working like it used to anymore. 
I think I paid about $90 for my PSA 9 Gyarados many years ago. I remember seeing Ninetales PSA 9 around that price too. 8s were in the $60 range. I don’t think they were ever as cheap as $30 (graded) but they were definitely in the sub-$100 range. This was probably around 2010-2013 when I first found out PSA cards were a thing.
It’s important to consider the state of the Pokemon Market when looking-back at price-point. I started-out on eBay back in 2009 and the Pokemon Market was MUCH SMALLER than it is today! There weren’t nearly as many collectors and/or sellers - to the point where you could at least recognize the User ID of nearly all “big” sellers. PSA Grading was just becoming a thing; with pricing all over the place (no real data to base pricing off).
To answer your question simply, the pricing was A LOT cheaper than it is today!!! I remember purchasing 1st Ed. Base C. / Un. Sets in NM Condition for $75.00 from ebirdman - and those could be purchased all the time at that price-point! I remember purchasing a PSA 10 Shadowless Charizard for somewhere in the neighborhood of $500.00-$750.00. Talking about those price-points today seems ridiculous; however, that was the standard pricing back in ‘09 and ‘10. Nobody saw those prices as being “cheap” - just the going-rate back then do to the smaller collector base and funds of that collector base.
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This is obviously the best answer. It wasn’t cheap back then, just like right now you’re not considering the prices cheap. In the years to come, when the prices are doubled what they are today, will you be looking back at todays market and saying look how cheap it is?
The cards were relatively cheap, just like they are today.
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All very good points. Another factor to compound all this is disposable income. For myself, I pretty much knew these $90 1st ed base cards wouldn’t last but I couldn’t buy whatever I wanted since I was in school and making little to no extra money. I originally settled for 8s because the $100+ 10s were just out of a reasonable price range for me at the time. Too bad, right? haha
The age group of people who first grew up with Pokemon were probably in the same boat as me and had little to no extra cash back then. I think the boom that coincided with Pokemon Go is heavily due to a lot of 20-somethings with real jobs and a fair amount of disposable income becoming re-interested in the collecting at the same time.
But yeah, to summarize, I mentioned I was interested in a PSA 9 Ninetales for $90 a few years back. I ended up paying something on the order of $400 last year for one. This may seem like a big difference but honestly, now that I have a job and income, $400 is probably worth the same to me today as $90 was to me 5 years ago. That’s the impact of disposable income.
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Going back to 1999, it’s safe to say I always bought and sold at close to market value. Yes, prices have fluctuated numerous times but that was always only recognizable in retrospect.
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Every time people romanticize past prices, These 3 points need to be mentioned:
- The market size was smaller
- Consumer income was less
- Even if you could buy the cards, you didn’t
The last one is the most important in my opinion. I was around and able to buy 1st Ed base cards for a fraction of their current price. Ironically I have purchased more in the past few years than any other time, for probably 10 times the price.
Point being, there is more value today. Probably a good video topic to discuss Price vs Value. 
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Purchased my Zapdos PSA 9 First Edition for 74$ in 2014. Sadly I did not buy any other Pokémon Cards at those once stellar prices.