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I already consulted Is it "less than" or "lesser than"? (but the answers are contentious) and Using "lesser" or "smaller" in reference to an abstract quality. Mod RegDwight's comment under:

Lesser is an adjective. Less is an adverb. Everything else follows.

Source: p 56, The English Legal System 2012-2013, Gary Slapper

In Fitzpatrick v Sterling Housing Association Ltd (1999), the House of Lords had extended the rights of such individuals to inherit the lesser assured tenancy by including them within the deceased person’s family. It declined to allow them to inherit statutory tenancies, however, on the grounds that they could not be considered to be the wife or husband of the deceased as the Act required.

assured is an adjective. Is this why lesser is the only choice? Why not less-assured or less assured?

https://english.stackexchange.com/a/24749 says "Less refers to quantity, lesser refers to quality."
Aren't we concerned with the quantity of the 'assured tenancy' here? So why not less?

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  • Can you be one assured, two assured or a million assured? Its about quality obviously.
    – JuliandotNut
    Commented Aug 25, 2014 at 13:59
  • It is possible that "lesser" is modifying "tenancy" directly. This might be an example with multiple "assured tenancies", one of which is a "lesser tenancy". Also, "lesser" sounds like "lessor", which has a completely different meaning. You might need to find other examples to figure out what word is meant here, let alone what it means.
    – Jasper
    Commented Aug 26, 2014 at 5:58

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lesser sense 3 (an adverb) and then less sense 5 "to a smaller extent".
Something like:

That is the lesser of two evils.

So it seems it is a quality measurement. I suppose you could use "less", however "the lesser" is referring to a member of a defined group (using "the").

Legal terminology may have standard ways of saying things, which I would not be aware of.

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In your example, you could indeed replace "lesser" with "less" - but that would change the meaning of the sentence as written.

To paraphrase: the "lesser assured tenancy" can be (and probably should be) read as "the opposite of the greater assured tenancy".
If it had been written "less assured tenancy" instead, it would read as "the not-as-certain tenancy", or "the opposite of the more assured tenancy".

The difference between "less" and "lesser" in this context would be something like the following:
A "lesser assured tenancy" is worth less money, and guaranteed ("assured"). A "less assured tenancy" is not guaranteed: there's a chance that the tenant might get evicted, or not be allowed to move in.

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