Gerda, it is impossible to answer the question you ask about worse, but whether something is actually worse or someone thinks it is worse are two different things. I can only point out some things I recall you saying.

1. If a sale is forced, and I have no way of knowing if the court would do that on either property, but presumably more likely on the vacation property, it would be at the market rate and you guys would presumably split the proceeds after all mortgages, fees, etc. You might even be able to point out how he has been with money/jobs and get his equity as an advance on his support payments. They do something similar to this in my state. You'd have to check with a NY licensed family attorney.
2. I got the impression you offered him more equity in the deal or a higher price than he would get in a forced sale.
3. Not that I know, but I think it unlikely he would get to call the shots for 6 months on the sale in a forced sale situation. The loss of control over the outcome could be very difficult for someone like him.
4. A new judge may want to stick to either one of you. No way of knowing.
5. A different judge could order him to pay more support if still open (unless statutorily set, and even then might set a higher minimum point) or find that he is intentionally under/unemployed.
6. An appraisal for a buyout could be much higher than he would get in an actual sale if he forces it.
7. Have you looked into the possibility of a straw purchase on the vacation property if you are that intent on keeping it? Is it a possibility where you are? You might end up being able to buy it for way less money than he would make you agree and not have to deal with him (although there are other complexities that have to be considered). Of course you risk losing it to another buyer, but that would mean more money in your pocket.
8. I'm not sure I know why you have to be in the city. I didn't get the impression you had a regular, show-up every day kind of job in a specific place. Could you make the argument that if you have to sell the house to pay him out, then you will have to leave the city? Would that give him pause? Have you and the lawyer discussed whether that is a special consideration for the massively expensive place where you live?

I don't think any judge is going to be very sympathetic to your desire to keep the main property if you can't pay him out his equity or you guys can't come up with a fair appraisal situation or get the financing. I think it even more unlikely that they would entertain arguments about keeping the rental property, even if it is an investment or income property. There is not a lot of sympathy about forcing the sale of investment properties.

I can't stress enough that the desperation you have to hold onto these houses, and thereby agree to something with a tyrant or at an inflated price or other undesirable term, jeopardizes your ability to come out with a fair price and an even distribution of assets. I just don't think the court is going to buy into your various schemes for trying to keep them. It is not what the courts are there for. In some states they make you sell. In some states they let a primary parent hold onto the house until the graduation date. In some states, like mine, they award the house to someone.

You will never know if he was willing to go to the mattresses or cave unless you walk away from what you have, and that just seems risky given how hard this has been for you, the limited resources to carry on the fight, and the distrust you seem to have for your lawyer and the legal system.

Please take your time. Think through everything. Try to come to grips with why it is so important to hold onto the houses. A house is not a home. You've made good investments before and you will make them again I'm sure. Try not to catastrophize.