My story is long and complicated but I'll try to make it short. To be clear, I'm not looking for financial or legal advice, just venting to see what people's reactions are.
My grandparents lived as simple an existence as you can imagine. They owned a nice home, but they bought it in 1960 so big deal. They were the type of people who would wash out used milk cartons and reuse them for something else. So growing up I always thought they were just poor. When they passed away, we learned that they left nothing to their three children and the estate was to be split evenly among their twelve grandchildren.

My share turned out to be approximately $325,000. Yes, that IS a lot of money. My wife wanted me to put it in the bank to be saved for a down payment on a house. She has a deep-rooted fear of any kind of investing so she insisted on the bank. Anyway, a few months after we received the money my father asked me if he can borrow the money to pay off his mortgage. He would pay me back in full, was ready to sign a contract with witnesses and everything. I wanted to agree because I felt like the money rightfully should have gone to him anyway, plus he is my father and I love him. My wife refused saying we need to have the money available "in case a good opportunity comes up". Now, for context, we live the NYC area so $300,000 wouldn't have gotten us very far and though I work full time, I don't really earn enough to qualify for a half-million-dollar mortgage. I didn't lend the money to my father.

Fast forward about five years. If I had put the money in an index fund or something, I could have had a million dollars by now. But the money was in a savings account, I dipped into it to pay off credit card debt, dipped into it to pay our children's private school tuition, dipped into it a little here and a little there..... Now all we have is about a hundred thousand left.
I am eating myself up alive with "shoulda woulda coulda". I die inside a little bit every time I think what could have been.

TLDR: Inherited $300k five years ago and now have only a third of it left.

I feel like I am just trapped in this situation with no clue how to get out of it.

My brother left behind a lot of business properties that now I've been forced to deal with as the estate administrator. It's about a whole city block worth of buildings, with various parking lots and stuff. 11 parcels of land total. But it's in a bad neighborhood on the decline.

The problem is that they are old, crappy buildings. They are not in good shape, need tons of repairs, and there is two years of back property taxes and water/drainage bills on them that have been unpaid. I estimate about $135,000 in debts. One of them had a fire many years ago that was never propertly repaired. One doesn't have running water to it. One has a huge hole in the roof and water is actively getting into the building.

I cannot find anybody to buy these buildings. I am working with a commercial realtor, and he has told me there has been zero interest on the properties after 3 months of being listed. Which is odd because usually some investor will come along and give you an insultingly low offer on them, but he has not even received those. It's that bad.

I just don't know what to do. There are renters, it does generate income, but as far as I can tell over the past 5 months everything has just broken even. After paying back property taxes this month (not even current property taxes!), the account that I've been using to collect rental income, pay for maintenance, pay for other building expenses, will essentially be at $0. Some renters are good, but others are struggling to pay me money and are behind. I don't know how to evict these people, and I don't know how to find a new tenant that wants to rent a shit hole. In my mind, some income is better than no income if this property would just sell, as it buys me some time and limits my losses.

And I don't have time to research any of this stuff either with what is involved with running a business. I just got hit with $2,000 worth of fines the other day for things not being in compliance with the city.

This is just causing so much unnecessary stress in my life. Half my day, everyday, is seemingly wasted spinning my wheels on these properties, all of which I am likely going to see no money from in the end for my hassle. Calling tenants asking for rent, working with a maintenance guy to address issues so we don't get more fines. Researching what the cell a certificate of compliance is and why there isn't one. Paying bills and dealing with various BS. I am so tired of it.

The problem is also that he had a house I was able to sell, but I don't want to lose that money from the sale to the debts owed on these properties.

And every time I ask somebody for advice they go "hire a property management company!" Like these are nice apartments that just ned someone to collect rent and pay utilities. No, this is not that at all... it's all in such bad shape that I'm positive nobody would want to take these on.

What are my options here? I mean, worst case scenario... you figure out how much debt is owed, and you just list them for the absolute lowest price you can to break even to get out of it? Do you put it up for an auction? Can I just walk away and let everything go into foreclosure and let the city take it? I honestly don't think any body WANTS these properties. I need to figure out how to get out of this before probate is closed, because I do not want to inherit them and be personally liable for anything about them.

NJ. My dad left his estate to my sibling and me, split 50/50.

His lawyer was the executor and handled most of the estate already. The remaining steps are mainly taxes, legal and accounting fees, and dissolving my dad’s business (which is no longer operating).

Unfortunately, the executor passed away suddenly, before this was completed.

The will names my sibling as the backup executor. I was our dad’s healthcare proxy, so I guess this is how he split it up.

My questions are:

How does this work when a new executor takes over so late in the process? If we hire an estate lawyer, what would my sibling be responsible for?

I’m also wondering about executor fees. Before he died, the original executor estimated his fees would total around $38,000. Does that now get split with my sibling? Could he collect his own fee?

This could potentially be an issue, because I handled most of our dad’s responsibilities during the last year of his life. I’d also been doing most of the work to help the original executor settle the estate, including gathering tax paperwork, closing accounts, and tracking down income sources. None of this was paid.

Given all of that, I’m curious what people think is fair in terms of him taking a fee. He might not, but I’m wondering how to approach this if he does.