This is a mess that I hope you will come out clean. My suggestion is do not give up your income source. Do not relocate your family till have a clearer picture All your assets are illiquid and you could find yourself in a cash crunch very easily. If you have lived in the US these assets are not representative of you. Try to dispose them slowly and reinvest elsewhere.

The hospital could operationally collapse without your dad and take it for granted the builder will try to take advantage when your dad is gone. Thats how India works !!

I suspect that most people on this sub won’t be very helpful as your situation seems very dependent on the vehicles, laws and regulations or lack thereof in your home country. I have heard of horror stories from Indian friends about how third parties try to take advantage of the situation once the primary person passes away.

I would consult an Indian real estate specific sub. Most of what applies to the US, Canadian or Western European market would probably not make sense.

My take is the nature of the assets (in India, illiquid, and tied to your fathers reputation) make those market values somewhat speculative. Given your family has medical issues and needs geographical flexibility, I would liquidate ASAP, even at a steep discount. You are what we call a "motivated seller" and I would get out of as much of that as possible quickly. I would focus on the assets outside of the hospital which is a different animal in that it's an operating entity and the $21m parcel which I think deserves special attention. The rest get out and get out quick

Your ancestor(s) built an empire, not your empire. Take it you have zero-to-little real estate experience, were not involved in the running of the business in India. Furthermore, business abroad is very tedious compared to US practices, both culturally and literally. The logical solution is to exit all and diversify

On the contrary, the positive thing about leaving heirs a RE empire is how difficult it is to exit. Most heirs squander inheritances, so having it locked up with only some cash flow is a genuine strategy. That said the 4% you inherited is a joke and my issue with real estate — if you are not actively managing it, making on-going improvements to your property, negotiating rents or using leverage, you end up getting wrecked against a 100% passive equities portfolio

Even if we call your total NW $35M that's already UHNW. Unless you are trying to own a yatch, fly private, or influence politics, you don't really need more than that. Hire a professional firm as short-term solution

It's going to be miserable for your father to watch his empire be sold off. Instead of a fire sale, I would cautiously prepare an exit. Start negotiations now, finding a good deal usually takes 2-3 years anyways and you want to line up potential buyers against one another. Pull the trigger once he passes. This of course puts aside the nuances of Indian tax and estate laws which I'm not familiar with. For your sake I hope he is not a U.S. citizen or resident then you have estate tax to worry about as well.

You can’t do this alone. Don’t even try. The money you spend on the right experts will be the best investment you will ever make.

You need to work with at least four types of local experts. And at this level of asset, they need to be the top specialists in their field. First, you need a commercial real estate consultant. Not a broker, a consultant who knows the market and how it works, which properties should be kept, sold, restructured, revalued, etc. The real estate consultant is the most important piece to your puzzle because he is the one who will know how to get this mess under control and manageable in the future.

Next you need a good commercial real estate broker or two, who are specialists in each type of property you decide to sell or restructure the leases on. The broker is not the person to help you restructure the empire, he is the person to execute what you and the real estate consultant decide.

The next two are obvious. You need a tax professional to smooth out the taxes and a lawyer to structure each deal properly.

Your dad is the only one who can keep all these balls in the air because they depend on his personal relationships with each part of the ecosystem around each property. Explain to him that his personal involvement is the thing holding the empire together and no one can do what he does because they don’t have his personal relationships. The next generation needs to convert his achievements into something they can work with, as he did with his assets, and use his empire to create wealth that will be used to continue his legacy, just in a more transferable form. You are not destroying his legacy, you are preserving it.

My wife had to clean up her father’s real estate (his home) in India. It’s a pain the ass. It took her six weeks.

Her mother’s real estate (commercial) she’s essentially abandoned given the complexity and realities of business in India.

(Notionals an order of magnitude less than yours)

If you have no affinity to RE and don't intend to get in the weeds, I would liquidate the assets and simplify. The elephant in the room is likely the $21m parcel.

It's also worth looking into the tax situation and what that would mean. If you have "prime" assets that you could somehow redevelop without incurring a big tax bill it might make sense to retain them even if the cap rate is low. Every city has areas that will never go out of fashion.

On the hospital I would see if a sort of management buy-in is possible to transfer ownership, for example by selling shares of the entity. If you have no experience running a hospital I don't see how that will turn out well in the long run. My MIL had a friend who set up a niche clinic in Latin America and when he passed, his brother took over, and seemingly it all went down the drain.

Personally I would make sure to get at least $20m out and invest in secondary assets (e.g. diversified stock market portfolio).

Liquid assets I would split between you and sister into own accounts, and illiquid such as property I would retain together.

Despite what others have written, I would not liquidate at steep discounts. But I would put some pressure to get the entire process going as that will likely take a few years to be able to exit at decent prices. Don't hold out for the best absolute price but be pragmatic.

Also keep in mind inheritance taxes for all of this and make sure you (re)structure things before the death of your dad. Not the most fun topic to talk about, but worthwhile when thinking about family wealth.

Are you and your wife US citizens? What is your income in the US?

Can sell some assets; capture capital then leverage into private lending notes—can structure amortized or paid annually—cash out refinance & do the same thing—way less emotional toll

Trust seems like a must in this scenario—holing companies in each state you are invested in; structure asset payment into trust & set regulations

Rockefeller method —great work & congratulations, good problems to have

I’m dealing with the same issues. The main issue if you live in America is that any real estate transaction in India involves a significant amount of “black” money which you can’t do anything with except roll into another piece of real estate. Unless you want to deal with what is basically money laundering.

No idea what I can do except wait and see if the system reforms over time.

At one point, I had seven pain in the ass rental properties several were commercial, now down to two rentals.

Sell the biggest pain in the properties, offer seller interest only financing which delays the bulk of the capital gains to when the loan is paid off. Slightly below market interest rates let’s you juice the sale price of the property.

I’ve put my extra cash and some proceeds from rental real estate sales into several top-tier mortgage funds which pay 8 to 9% per year.

Life is much better now without the stress of so much rental real estate.

My biggest headache would be the hospital.

Without knowing anything else this feels like a passion project of your dads so unclear if selling that off first is a nice homecoming moment. But strategically I would.

I was in a similar situation but with assets overall mostly a bit cleaner. My plan coming in was selling quite a bit of it but once I worked myself through everything I ended up keeping most as the cash flow was much better then the exit price (low multiples). The structured I didn’t replace much eventhough that was the plan coming in. In the end even that $ of real estate is still manageable without enterprise like structures. Especially if it’s large assets (as opposed to 700 flats across 200 buildings) and quite a bit of land.

If you can sell either the 9m building or the large land deal (unlikely as it is being developed right now) you can diversify enough. Would do that year 1. then you have time to figure out the business and wether you want to spend more time working on it or exit everything on like a 3-5 year plan

Is all of this real estate in India?

You are the textbook case for a 721 UpREIT

I couldn’t tell by your post if the assets are stateside or overseas. I cannot speak to overseas

However, if stateside, this is exactly what a 721 is for. It’s the lesser known cousin to the 1031

In practice, you can contribute real estate assets to a REIT in exchange for shares of that REIT

This contribution is tax free, just like a 1031 is

The benefit to you, outside of the taxes, is you move to passive REIT investor vs active owner. You are also more diversified since you now own a piece of everything the REIT owns

The downside is you lose complete control and the REIT can do whatever they like with the underlying assets.

It’s typically most appealing for folks who have built a large portfolio and no longer want to deal with it but still want steady income exposure