My question is, how likely am I to be able to win a suit against him to continue alimony for me, for three more years?
That depends on the specific terms of your alimony agreement. If it states alimony is not subject to modification (non-modifiable) then you don't have a strong case. The court allows both parties to freely and voluntarily agree to such terms. The court will not modify an agreement that was entered freely and competently by you unless the agreement permits modification. You accepted the five years voluntarily. A divorce judgment is considered final unless you can show you were not of right mind or were coerced
into such an agreement against your will. Based on the information provided, that does not appear to be the case.
Now if there is no restriction regarding modification, then you can file based on changes in circumstances requiring more support. If you are not able to live on your own without his support, it is possible. Again it would depend on what restrictions there are in terms of modification.
As to healthcare, that ends upon agreement. It is not subject to modification as spousal support
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