Indifferent.
Although young me would be tickled to know I still talk too much and over explain.
I like to give past me the benefit of the doubt.
"Give past me credit. He makes a decision using the best available information at that time. Retrospect is always right. But it already knew the outcome, so how fair is it to judge?"
Several forums, websites, IRC channels, and BBSes I used to frequent increasingly disappear as the decades have passed.
I continue to preferentially peruse 4chan vs reddit. Granted, reddit didn't exist for a long time while I was posting away at 4chan. At this point at least over over 10-11k posts between the various sites and the angry void that is the Internet.
I don't consider it time poorly spent, though. They were thousands of posts that represent my little social connection to the world, as insignificant as they are. Exchanges of ideas, discussions of projects, personal struggles, or of irrelevant nonsense, all of which form the aged, apathetic asshole that I am today.
Financial position is a fair bit better than expected.
On top of a reasonable salary, I had the opportunity early on for real estate and rental properties. Leveraging the equity from them and the alternate income streams has been very beneficial. It gave me the financial freedom to also get into investing in a long term manner. I'm one of the only members of my extended family to have established a very solid long-term financial plan and an actually diverse financial portfolio.
Career-wise, I'm an experienced telecom engineer now. Which is about where past me expected to be in my middle age.
I'm paid reasonably well for the level of responsibility I have. AI will probably eliminate my job in a few years, so I've debated pivoting careers to feeding the data center monster.
I've been told I seem to enjoy teaching and training, but YouTube exists so I see no reason to waste time pursuing it.
Close personal relationships never happened.
This won't surprise past me at all. It was an eventuality that I accepted as far back as early high school. The women that I was attracted to never considered me a candidate to begin with. Add that the few that were attracted to me, I didn't find any physical attraction to, as well as having personalities that could be simply categorized as aggressively toxic.
I will admit that outside of my direct family. I have very, very few friends. I have never experienced close interpersonal relationships in any way, shape, or form. Sex? I haven't even held hands yet. Let's not go getting ahead of ourselves, now.
Past me would probably say that I'd at least expected to have paid a prostitute before hitting 40 a good while back. Well, in all honesty I can't say I didn't try: I guess I gave a bad vibe on the first attempt. She left quickly and didn't even take the cash. The next attempt, the woman took the money and ran. Both times I ended up walking to nearby liquor stores and drank myself to sleep.
Yes, there was crying.
I admit that past me would probably find my current living conditions opulent.
Past me expected to maybe own a townhouse or condo at best. I live alone and work from home in a fairly large house + basement tucked away in a quiet street off a highway in the mountains. Little hobbies keep my sanity because I have no real community connection. While I love Southern Appalachia... I will admit that in this area a random, white collar, Asian man is a "tolerated" minority at best. Heckled if it's a bad day. And I learned to carry a gun all the time in case of the worst. Which I've had the misfortune to have had to deploy twice in my lifetime so far. I do wish they (the police) made it easier to get those guns back after they're done with it as evidence. I still haven't gotten either handgun back.
Health-wise I'm worse than I thought I'd be.
But given my family health history on both sides, I can at least say I'm here. Chronic pain, several unexpected hospitalizations, associated surgery complications, and insomnia for the past decade and a half. Most of it you learn to deal with, but the insomnia? Try sleeping 3-4 hours a night at best for a decade. Benzos and Ambien make me sleepwalk in a bad way. Orexin inhibitors are prohibitively expensive. Over the counter stuff is what I have to work with.
Oh and later in life, both sides of the family consistently lose their minds. So I'm just waiting for my turn.
Past me would probably wonder why I have so many guns though.
Past me was also incredibly naive. One it's for self-defense. Learning to operate a few types proficiently hedges your bets if you end up with an unfamiliar firearm in a bad situation. Two, it's just a fun hobby. A little expensive though.
I have so many that it's easier to buy ammo in bulk by the thousand in some calibers. Since I go through probably 2k rounds a year. Mostly 9mm and 5.56mm NATO. It's fun stuff. I am not a good long range (150+yards) shot though. That could use some practice and my reloading presses could use some more use, especially my 300BLK dies.