1. We are renting it at market and that covers the mortgage and maintenance. We had an assessment in place for about a year to cover major rennovations to the building which have resulted in appreciation.
Exactly....the problematic assessments. That being the case, you're relying on appreciation. There are no guarantees, but on the UWS of Manhattan, there's a pretty good chance that the value will keep going up.
2. We could do improvements, but I am not sure whether the increase in rent would justify it. Our neighbor gut rennovated her unit and she rents her place out for the same amount we rent ours.
In that case, I think it's safe to say your cash flow problems aren't going to be fixed any time soon.
3. Liberal sublet policy meaning we can rent out the place for as long as we like without restriction as long as its not a short term rental i.e. airbnb. This is unlikely to change as the sponsor owner % is high.
Has the sponsor been selling any shares lately? Without knowing the exact details of your specific co-op, I'll just say that you never know when a sponsor might want to sell some, most, all of their shares. Connected with my hatred of assessments as they pertain to investment properties is my belief that no matter what, you're putting your investment into someone else's hands when you own a co-op or condo.
5. Depending on the area, instead of owning one coop we could buy anywhere from a duplex to a fourplex in California if we invested all of the money from the sale.
I'm partial to spreading your costs and risk among as many potential tenants as possible. Therefore, if you could get a fourplex in California with higher cash flow, that would be my vote. Not only would you have more control, but one vacancy isn't 100% of your income gone.
6. We don't need the cash flow now but ideally we would like a place that cashflows and appreciates. One thing thats attractive about owning a property in California is that we are not obligated to pay maintenance to a coop which eats from the cashflow, however, that said we realize there will be maintenance expenses associated with owning any property.
While there will be maintenance costs, they'll be a lot more under your control, and, as I said above, you can distribute them among more tenants. Again, though, if you're playing the appreciation game, I'm the wrong one to ask. I can make guesses about what the markets are going to do, but others are far more qualified than I am. I don't think NYC is going anywhere, but you just never know.
8. Coop does not have a flip tax.
For now.
9. Can you elaborate on your philosophy of never selling. Would you sell to buy something bigger? We could do a cash-out finance in a few years to buy another MF
I guess I mis-spoke when I said never sell. I just mean that there are far too many instances I've heard of where people sold because they thought their property was going to be worth less later than it is now, and they ended up missing out on a lot of money. If you hold anything long enough, the odds are that it's going to increase in value (I know, this goes against my entire non-appreciation advice). I would sell to buy something bigger if there was no way I could do both. If you could find a value-add property in California, BRRRR, and buy another property, etc., I think that's an excellent strategy, as do many on this forum.
Again, anything I can do to help, please let me know! Or if you'd like to talk privately, my offer is still open.