Stop investing and start collecting. Like this the future value of your cards don‘t matter 
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@trainerdlyellow 10 years ago, Scott struggled to earn $250 or so for PSA 9 1st Edition Base Charizards.
I get what you’re saying… You’re not going to net the same ROI of buying a box for $100 10-20 years ago. However, you could say that about pretty much anything. Will you not buy a house for $500,000 because it was $10,000 50 years ago? 
I think there are some opportunities to be made in this hobby. It shouldn’t be too hard beating inflation, but there’s obviously no guarantee. You can’t really treat collectibles like an investment. If you don’t wanna risk it, just put your money somewhere safe at 3-4%. 
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I don’t think this is a good way to think. I don’t think you’ve missed the boat, there are plenty of ‘investable’ things in pokemon some of which are ‘expensive’, you just have to assess what you’re buying and work out if the growth potential/risk aligns with your goals & comfort level. There are a lot of people, myself included that have bought and are currently buying things confidently for 4/5 figures and expect to see significant growth over time. I personally am very risk averse/conservative with what I buy as well, and I’m not concerned with how much I’m paying for certain things.
I could do that list pretty easily (less than an hour) as a page on pokemonprice.com 
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There are hundreds if not thousands of collectors today that were not consistently collecting years ago (a lot of which are on this forum) and are now spending thousands of dollars on cards or sealed product.
I was a collector in 1999 (when i was 5), stopped in my teens and picked up collecting again in 2012 when i had an income from working. I still consistently spend thousands each month on Pokemon and will continue to do so now for the rest of my life (I am 24 fyi).
I will continue to earn more money as I get older and I assume there are many more people like me that will also never stop collecting, which is why I am not scared at all about the longevity of this hobby. As long as as Pokemon (the highest grossing media franchise) is doing well and collectors like me still exist, the health of this hobby long term will only continue to grow.
Collector: Buy what you like.
Investor: Do your research. Older, Minter, Rarer, Scarcer, Iconic etc etc. Do not rush to sell.
-Luke
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Thank you all for your insight. It is appreciated. Obviously, there is a lot I still have to learn and I’m going to need help. We can’t all chase a PSA 10 'zard of course
I took Scott’s advice a year ago and got a part time job to finance a my continuation in Pokemon. It’s only been recently that I have thought about investing. As stated earlier, I am constantly bouncing back and forth between doing this for fun, and making this part of a long-term investment strategy. I’m sure many of you can relate. I want a high grade first edition Base Set for no rational reason. I’m simply fulfilling a childhood dream. However, compromises have to be made. At best I might bring home 10k from my part time job, annually. I don’t see PSA 10s in my future, needless to say. So, I’m speculating on other opportunities.
I have this theory that as more people enter the hobby the supply of highly sought-after PSA 8, 9, and 10s will dwindle as they will most likely be in personal collections, or just out of reach for most. A few will make it to the market here and there but possibly not at the rate or frequency they do today. This may make PSA 5, 6, and 7s rise in value, as they are easier to obtain for the new entry into the hobby. Of course, these are all the highly speculative ramblings of a noob, so be advised
But anyway, I’m curious. How would you start investing if you were starting out today?
Your “theory” isn’t really a theory. Just logical thinking
Also… Investment advice is never free!
Research, research and more research.
One idea I always dispel is “first to market”. The reality of that statement is, “taking a ton of risk”. Naturally everyone I know who was “first to market” genuinely enjoys pokemon. This is why I always advise to genuinely enjoy the hobby.
Also, the old prices need context. No one was around. You couldn’t liquidate cards like today. Hence why there was so much risk. Today has the least about of risk, but that doesn’t mean everything you buy will increase. Ultimately no successful investment of any kind is easy. Sure people like myself, Gary or others who were first to market have an advantage. But that is only because we decided to pull the trigger when everyone else was too scared.
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That’s it right there!
I’m terrified that I’ll loose big if I gamble now. Even without Captain Hindsight, I could have bought a graded Base 'zard 10 years ago. But my interests had shifted and I wasn’t paying attention. Lesson learned.
Just do what you want man! No one is always 100% right. The best advice anyone can give is simply collect what you enjoy and spend within your means. Even if prices drop, you still get an emotional utility.
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I don’t think it’s because others were scared. It’s more likely that people lost interest in Pokemon while growing up and are now gaining that interest back again and starting to collect.
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Make sure your financial house is in order before “investing” too.
I know a lot of people who are constantly on about the latest and greatest “investment” opportunity. Crypto, AAPL, some pennystock, Pokemon, whatever it may be they are just in it for the money and have no knowledge of the various markets. On top of that, and worst of all they gamble er I mean “invest” with money they need for their day to day livelihood. If you buy XXX today for $500 and in two years it goes to $1,000 you haven’t made anything if you’ve carried it or other things on a 20% interest credit card the whole time and I think people fail to see that often.
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Op, I don’t advise to buy low grades. You also don’t seem to have the capital to invest in sealed product or PSA 10 cards, etc… so what I would advise you to do is just spend what you can afford on good deals you find now and then.
You could also collect things like PSA 9 holos which are about $20-50 most of the time. While I don’t see them as a great investment, I don’t see the price drop any lower.
Either that or buy something big every 3-6 months. Up to you!
The amount of people in debt over a collection is baffling and just plain sad.
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The whole world is in debt. It’s way too easy to get credit and even easier spending it… especially now online/mobile. One click of a button could cost several thousands. It’s dangerous.
I know that I myself have a credit card limit way higher than I should, which put me in a lot of gambling debt I’m still paying off.