Welcome to Fluther.
As a medium-term resident of Connecticut, myself, all I can tell you about Connecticut probate is that no one can predict outcomes with any degree of certainty. Probate Court in Connecticut has long been known for its provincialism – the wide variation in administration from one jurisdiction to another – and for its equally varying levels of professionalism. And that’s before we get to its outright corruption in some cases. (I won’t link to them here, because as a resident I don’t want – seriously! – anyone involved in any of those cases to link back to me and make accusations of libel because of the things I might say.) But I think the cases are well known enough (since I read about most of them in the Hartord Courant, after all) that you can find examples of your own easily enough.
Even when the processes seem fair and reasonable, and even when the judges (and attorneys in lieu of judges in some districts) are honest and competent, and even when the general administration seems to run as it should (sort of), decisions can take years. Literally, years, even for what seem like cut-and-dried cases sometimes. (And those years cost money, as estates can be billed for all administrative costs that are in any way related to the case.) It’s a notoriously awful system.
The opening chapter of Dickens’ Bleak House represents the Connecticut probate system pretty faithfully, even if unintentionally.
It’s not even a case of “who has the better lawyer”, but sometimes a case of whose lawyer has the better access to the judge or other administrators. (At least, when there are axes to be ground, costs to be assessed and oxen to be gored.)
I also have zero legal education, and I am not even familiar enough with the ins and outs of inheritance law to offer any kind of opinion on the efficacy of this will (if it even is a will). However, if I wanted to contest it, one of the obvious points of attack is as to the mental competence of your grandfather’s partner, in the first place, and secondly any degree of coercion which might have been applied (by you and your brother, for example, or any other family members) while she was in the rehab facility.
As a practical matter I would suggest simply speaking to the woman (your great-aunt?) to see if you can plumb her feelings in the matter and resolve any issues amicably between the three of you (or the four, if you count your grandfather as well as yourself and your brother as the “official” heirs). Another point of attack is what consideration was extended to the woman in the will if it were left uncontested. If she gets nothing either way, then what’s the worst case scenario to her if she contests the will?
Composing members:
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