DH has recently been getting some inquires from other businesses interested in buying his business. Up until now he has not been interested but he is tired of the stress and if people are wanting to buy in this economy.... He wants to work this year on getting it ready to sell, he has hired a company that comes in and prepares it, lists it, etc...
My issue is that DH has very strong opinions about what we should do with that money if the company does sell. We own 3 houses, we never intended on having this many, 2 are rentals, but rather needed to move to various towns and then didn't want to sell yet, but then the market tanked and we still have them. I don't want them, dealing with them is a PIA for me, I just want to sell. He want to pay them off, and if does sell his company then we would be in a position to pay off all 3 and still put some money in the bank. I don't want to remain in our current house forever, and neither does DH, so to me it does not make sense to pay it off when ideally we would sell and move in-town. I don't want the bulk of our money tied up in real estate, I would rather have it in the bank. I am trying to talk him into selling the two rentals, I am fine holding on them until the market gets better. We do live in a high COL area, prices haven't dropped that much, some, but not much is selling. Those would be gone, then maybe selling our current house, buying one that we DO want to remain in for quite some time and maybe putting half down and then doing a combo of safe investments, some cash in bank, and some other things for the rest of the money. We have no retirement saved because DH always sunk all the money back into the company and I think this is the prefect time to smartly set us for the rest of our lives. DH on the other hand has this vision of being completely debt free, he doesn't want to owe a penny to anyone, and while I get that, I am not sure if it is the wisest thing to do.
Even though this is hypothetical at this point, I need to plan because he is so set in his ways that it could take years of talking about it to get him to come around to any other position other then the one he currently has.
Any words of wisdom? 
My issue is that DH has very strong opinions about what we should do with that money if the company does sell. We own 3 houses, we never intended on having this many, 2 are rentals, but rather needed to move to various towns and then didn't want to sell yet, but then the market tanked and we still have them. I don't want them, dealing with them is a PIA for me, I just want to sell. He want to pay them off, and if does sell his company then we would be in a position to pay off all 3 and still put some money in the bank. I don't want to remain in our current house forever, and neither does DH, so to me it does not make sense to pay it off when ideally we would sell and move in-town. I don't want the bulk of our money tied up in real estate, I would rather have it in the bank. I am trying to talk him into selling the two rentals, I am fine holding on them until the market gets better. We do live in a high COL area, prices haven't dropped that much, some, but not much is selling. Those would be gone, then maybe selling our current house, buying one that we DO want to remain in for quite some time and maybe putting half down and then doing a combo of safe investments, some cash in bank, and some other things for the rest of the money. We have no retirement saved because DH always sunk all the money back into the company and I think this is the prefect time to smartly set us for the rest of our lives. DH on the other hand has this vision of being completely debt free, he doesn't want to owe a penny to anyone, and while I get that, I am not sure if it is the wisest thing to do.
Even though this is hypothetical at this point, I need to plan because he is so set in his ways that it could take years of talking about it to get him to come around to any other position other then the one he currently has.
Any words of wisdom? 
