Hello Ray Hayward,
Pleasure to hear from you! The correct answer to your 1st question is that I do not know, -whether a lien holder can do an environmental study to protect their lien, but a lawyer familiar with your State laws should be able to tell you. However, since the owner of record has died and no probate has been done, it is difficult to picture anyone complaining about an environmental study being done on the property. Without a court appointed administrator or executor, who would have standing to sue you?
Perhaps consult an attorney, but I'd be inclined just do the environmental study without buying any one's lien. Then I'd use anything negative found in the study to convince lien holders that their liens are worth even less than they thought.
If the widow has no plans to do anything with the property, she may complain about you trespassing on 'her' family property, but what are the odds that she'd file a lawsuit? Even if she were inclined to file, she has no standing to complain of trespass on a property that she doesn't own. Check that with your attorney. I doubt that you'd need any legal cover. It may be cheap enough to buy a junior lien. But, unless an attorney can give you a clear and well reasoned statement of some likely and adverse result from trespassing necessary to do an environmental study, I'd just do the study like I owned the place.
If one Environmental company won't do the study without your name on the title, find another. If you can tell a decent story, you'll find an Environmental Co. that will do the study without verifying the details of ownership.
As to your second Question, "if I convinced the Town to foreclose, would I be able to circumvent the Bank Lien #1?"
Verify when the 1st Mortgage (and each lien) is beyond the Statute of Limitations. See https://www.nutter.com/trending-newsroom-publications-Statute-of-Limitations-for-Mortgages-Referencing-Maturity-Date-of-Underlying-Debt-04-17-2015 If the date the 1st mortgage becomes due in full is specified, or if the underlying note specifies a due date, then the mortgage is only enforceable for 5 years past the specified date. You mentioned above that the 1st mortgage was only for 5 years and could be already unenforceable. Verify that with a RE Attorney. If no date is specified, in either the mortgage or the underlying note, then Mass Law presumes that the mortgage runs for 30 years from the date it was initiated. It is then enforceable for 5 years after the mortgage end date (35 years from the start date).
However, also be sure that you understand the effect of the Town foreclosing its tax lien. In my state, WA, when our county forecloses its tax lien, the buyer at the tax foreclosure auction gets a deed to the property free and clear of all previous liens. The prior mortgage and/or liens are wiped off the title. If a lien holder wants to protect their interest, then the lien holder must pay the property tax. Brother, I'm unfamiliar with Mass. laws and tax foreclosure, so that is also something to check with a local RE attorney.
Good luck