Betteridge’s law of headlines says any headline that ends in a question mark can be answered with no.
If you don’t feel confident in it. No. You clearly don’t feel confident because you had to ask so no.
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I think there is good advice in here, but you also have to consider other people’s goals, financial situations, and attitudes to the hobby when heeding their advice.
If you can’t be bothered reading everything below, I think @Dyl almost always gives good advice on the threads they comment on and this is true here as well. Their input is the most progressive, with @banks’ being the most thoughtful.
Generally, I think these types of questions aren’t the best to ask because of the aforementioned considerations. For example, I’m quite bullish and try to buy every week, however that isn’t viable for a lot of people. Many do not have that financial freedom, and those who do won’t all stomach the prices of today’s market.
Also, (most) people in here aren’t financial advisors – they’re people who collect cardboard. Some make fundamentally incorrect financial decisions on a daily basis, whilst others are millionaires. The point I’m trying to convey is that there is considerable variability in how people will respond.
Betteridge’s Law of Headlines, as was mentioned above, is not particularly applicable here either. It’s a journalistic term used to characterise something that is being sensationalised for traction. It supposes that anything with a question mark is not a definitive yes, and is exploring doubt to engage readers. We aren’t talking about a murder case, nor are we talking about something that has a clear, direct no. Your circumstances are wholly different to anyone else on this forum, so your answer will also be wholly different.
I think if confidence is an issue, I’d ask yourself where the lack of confidence is stemming. If I were to guess, I would say you aren’t confident in it due to your age, @Vertemes. Funds are far more limited and meaningful to you, because they cannot be easily recouped. From what I’ve seen you comment on, you believe in the product and its long-term strength.
You comment on modern, so I’ll touch on that a little from my perspective. I’m far more bearish on Modern, and would only buy singles I personally enjoy (see CHR FAs). Otherwise, I’d just buy sealed. This is because I don’t value modern singles. Any modern single I buy I value at $0 in my head and simply buy for personal satisfaction. Sealed is different of course.
Then, you have to consider that for new entrants into the hobby, Modern is easily the most accessible thing and what someone will naturally reach for at first. Modern being available can act as a barometer to gauge market interest for modern (and interest in Pokemon), but it doesn’t necessarily indicate broader market interest due to it being a key point of entry. A lot of the WOTC/Old Back buyers are the same buyers we had years ago, with there being a sprinkling of new collectors that filter through as well.
This is my own opinion and experience, but newer collectors are less inclined to spend large sums as their confidence level is lower, both in the product and their own understanding. They might spend large sums on a number of products, but there is generally a hesitancy to spend it on one single item. Over time new collectors either become “seasoned” and their understanding and interest will grow, or they’ll flake and trickle out of the hobby as their interest wanes. If you follow this logic, Modern will always be the most liquid with the highest availability due to turnover in collectors, even if print runs were to be lowered.
Lastly on Modern – the prices are not so monolithic and unachievable. If you wait, a $150 card is not magically hitting $1,000 overnight. You will see the shift happen and you can action yourself accordingly. The “risk” of buying now is also lower on Modern, because if you pay $150 for a card, it can only drop so far. It’s not going to $0, and even if it drops to $110, that isn’t completely detrimental – especially if you were buying it for your PC and didn’t intend on selling it anyway.
In my opinion, scalability is pretty relevant in Modern. Frankly, a $20-40 swing for a modern card means very little if you’re talking about picking up a singular copy. Those swings are primarily felt when you’re talking large quantities. If you have vintage goals, I would prioritise those as they are subject to larger swings and scarcity.
Keep in mind also, we’ve already reached the point where collectors who grew up with WOTC have disposable income. We’ve passed that point in fact. Collectors who are acquiring disposable income now are more in the category of the ex-era and beyond. Make of that what you will, Vert.
There are always people who believe prices are high, hold-off from buying, and then are ultimately priced out. Their personal opinion is valid and neither correct nor incorrect – it’s true to them and their circumstances. However, the market does not care whether you think something is priced fairly or not, and your opinion holds no bearing on whether we see growth or decline. For some cards, one significant sale is all it will take if they are scarce enough.
(People will say yes their opinion matters because they make up part of the market – blah – blah. Unless you’re a significant mover and buyer then no, your opinion really matters very little).
Just a little anecdote for you as well:-- Pre-2020 I chose not to purchase a heavily damaged Trophy Khan for ~7k. I technically had the funds but it would have been extremely financially restrictive. People would call you insane not to pick one up for that price now. Yet, at one point paying thousands for a card was essentially lighting your money on fire.
Make the decision that is right for you. If you believe you can afford a card, can incur the cost and be fine, then I’d say go for it. You’re young – that’s the best time to take risks and gamble on yourself. Just do your due diligence, be smart, and you’ll be fine 
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