Under Massachusetts General Laws Chapter 208, Section 34 there are at least eighteen factors judges at probate a family court should consider when deciding whether one party will receive alimony.  Here is the relevant portion of that section (with numbers added by me):

In determining the amount of alimony, if any, to be paid, or in fixing the nature and value of the property, if any, to be so assigned, the court, after hearing the witnesses, if any, of each party, shall consider (1) the length of the marriage, (2) the conduct of the parties during the marriage, (3) the age, (4) health, (5) station, (6)occupation, (7) amount and (8) sources of income, (9) vocational skills, (10) employability, (11) estate, (12) liabilities and (13) needs of each of the parties and the (14) opportunity of each for future acquisition of capital assets and income. In fixing the nature and value of the property to be so assigned, the court shall also consider the (15) present and (16) future needs of the dependent children of the marriage. The court may also consider (17) the contribution of each of the parties in the acquisition, preservation or appreciation in value of their respective estates and (18) the contribution of each of the parties as a homemaker to the family unit. When the court makes an order for alimony on behalf of a spouse, said court shall determine whether the obligor under such order has health insurance or other health coverage available to him through an employer or organization or has health insurance or other health coverage available to him at reasonable cost that may be extended to cover the spouse for whom support is ordered. When said court has determined that the obligor has such insurance or coverage available to him, said court shall include in the support order a requirement that the obligor do one of the following: exercise the option of additional coverage in favor of the spouse, obtain coverage for the spouse, or reimburse the spouse for the cost of health insurance. In no event shall the order for alimony be reduced as a result of the obligor’s cost for health insurance coverage for the spouse.

As you can see, several of the factors spelled out in your question are listed in Section 34.  I will assume you know that, given the circumstances, the amount of money involved, and the presence of kids in the marriage, you should certainly find a MA family law attorney  to discuss your situation.  He or she will be able to look at the specifics of your situation and give you a better idea about your likelihood of collecting alimony.  Good luck.