I struggle with this as well, especially as it related to pre and post COVID prices. I don't resent anyone, but I struggle with "why not me too?" I deeply regret and spend a lot of time ruminating over the things I did not do that I could have done to be better off financially. I was listening to the "Living with Emunah" podcast and he mentioned something that's been helping me with these thoughts. Essentially, he said "don't look back in regret, or you will turn into salt like Lot's wife." I hope it at least helps to know you're not the only one struggling with this.

I bought a house post covid and have a similar struggle. I'm not a jealous person. It doesn't bother me that others have more money and have fancier things. But that I'm paying so much more on my mortgage for a smaller house really eats at me

I'm gonna follow the anonymous trend for some reason. 1st of all Mazel Tov! 2nd of all, that is really hard. I see that in my family as well, the sibling who paid 450 for his house 10 yrs ago, the one who paid 450, 4 yrs ago and the one who paid 750 this year. (Yes, the last 1 has the smallest from everyone.) Something to keep in mind, in 5 yrs from now anyone who bought after you will feel the same way. Hatzlacha!

Trust me, this deeply eats at me. I think about it every day. I feel guilt because I feel like I cheated my child out of a better future. There are a lot of days that I feel like this decision is what ensured I won't survive whatever economic crisis is coming. Your post helps me a lot, because sometimes it just helps to know you're not the only one thinking or feeling something. Good luck to us all, may we each find our success.

This is such a common feeling. I think it addresses a theme that runs throughout our lives. There are so many situations where we feel like if we'd done something different, we could have drastically improved our life trajectory. I try to remind myself that I do my best. I was working with a limited set of options, and based on the resources and information I had, I did my best. It may not seem like the best outcome, but it was the best based on what I was working with, based on the situation Hashem put me in. It's ok to feel upset about it. It's upsetting. But you did your best based on where you were.

I think there's a uniquely Jewish trauma response aspect to this too. "I didn't foresee the future and make the right decisions so I won't survive the next pogrom"

We waited almost 10 years and have now given up on buying something big enough for us to live in. Trying to buy something small on paper to rent out, just to get on the property ladder. Yes we'd have made a huge profit buying a few years back, but we're focusing on just looking forward.

(this is in Yerushalayim)

So not looking back, but looking forward, would you advise others, even your children to push themselves to buy before they are financially "stable" in Israel, or to wait. I personally bought before, and had some hard months/years, even some missed mortgage payments, but looking back 20 years later, I would never have bought a house. About 5-7 years later rent (we rent out, and rent to live in) was more than the house mortgage, so the pain was only for a few short years looking back. To my kids I would tell them to push and buy right away, and just rent smaller until they could afford it, but this not what they preach on frum.finance. I just don't believe there is any other way in Israel, unless you make it big, or got really lucky with some investment.

Are we jealous when someone is 6"0 feet tall and we are only 5"6? Generally not. It is not the answer we want to hear but its a lack of emunah and understanding the grand master plan. There is a reason why you are looking at them but always remember there are also people looking at you longingly wishing they had what you do.....

It's only if you are investing the difference.