Thank you for entrusting us with this important business question of yours.
I will attempt to answer each part of it for you.
First, let me point out as an initial matter that if you were receiving a 1099, you were technically not an employee of the company but rather an independent contractor. An employee would receive a W-2 form, but that doesn't really matter for this analysis. Just for the record.
Second, as to the sale of the truck, you say that you put in equal amounts of money to buy what we will call Truck A and he put in his own money to buy Trucks B and C.
So, if this was done properly, the corporation should have debt to each of you for the amount of money that you put in for the trucks.
The board of directors
needs to make a decision as to which truck to sell. Once that decision has been properly made by the board, and the sale of one of the trucks authorized, the debt should be repaid to the party that provided the money for the purchase of the truck in the first place.
There has to be a fair decision about which truck should be sold. The entire board must make that decision after discussion and analysis of what is in the best interest of the company, not who should get repaid first.
Then, as to the dissolution of the corporation, the rule is that all of the debts of the corporation must be paid off first, and then whatever money is left over should be distributed among the shareholders
So, in this scenario, the corporation would have to repay each of you for the money that you put in to buy the trucks (or distribute the trucks in kind, i.e., give each of you one or more of the trucks, depending on how much it is worth) and then any remaining assets of the company would be distributed according to the ownership percentages that you indicated.
I trust this is useful for your purposes. Please press the green ACCEPT button. Thanks.