You asked a question: "how do I deal with this?" You deal with it by understanding that the most important thing is to be happy, and getting into Penn is no guarantee of happiness. You also deal with it by being realistic. Your list has two matches and two safeties. You KNOW that reaches are a long shot. You KNOW that matches don't guarantee acceptance. So are you truly going to be happy with possibly only two choices?
By applying to so many reaches, you have put a ridiculous amount of pressure on yourself. You haven't given yourself a chance to feel at ease because you set your own bar so high that it might not be possible to get over it.
The minute you graduate from high school, you will understand that you never have to deal with 99% of those people again. That's a good thing. Going forward, you will have more autonomy over who you choose to spend time with. Choose a couple of other match schools to apply to that you can afford and would be happy to attend, so that you have more options. Matches do not always come through. They are not safeties. There are hundreds of colleges where you can thrive, find like-minded people, find opportunities, be challenged, and be happy. There are many, many successful people who have attended no-name colleges. Do not assume that if you get into Penn, all the other students will be smiling ear to ear. There is a strong correlation between a school's selectivity and reported rates of depression/anxiety, etc... Correlation doesn't equal causation, of course. Just be sure to give yourself options. I have yet to see a student on CC complain because they have several good options to choose from, but I have seen dozens who complain because they are left with one, (or none), choice.
I have had the same issue that others report, and it does seem to have just started recently.
I often flag posts first thing in the morning. The Chinese ones, and advertisements that appear overnight. It is annoying to not be able to flag them more frequently than every five minutes. Maybe there could be some kind of feature that would allow reliable posters (maybe with 1000 or more posts?) to flag posts more frequently?
Another thing that might be useful: I am sure mutiple users flag the same post. Maybe mods have a way of seeing it, but it might be useful for a flagged post to be highlighted in some way so that other users don't have to do so. Sometimes I just comment with "flagged." @CCadmin_Sorin
OP, you've been posting for a couple of years already, if memory serves me. There are valid reasons for placing kids in public schools, such as lack of challenging coursework, being bullied, and the like. My son attended a private school from grades K-2, but our public school has much better resources for his learning disabilities, so he went back and has thrived ever since. His current UW GPA is 92 as a HS junior, and he is dyslexic and dysgraphic. He takes AP and IB courses.
I don't think putting kids in private school to hopefully give them an advantage to get into a top-tier school counts as a valid reason. Then again, it's your money, and you can spend it as you see fit. But here's a question: what happens if your children go to private school and don't get into tippy top colleges? What if they aren't interested in tippy top colleges? Would you be disappointed? If so, then you might need to examine your motives for sending them to private school if you have a very good public school already.