As far as your
silly experiment, your problem arises in that
ly is used to convert an adjective into an adverb, with the definition "in a [adjective] manner".
sillily is a word ("in a silly manner")
As far as "in a sillier manner", there are two rules for forming a superlative from an adverb. If the adverb was formed by adding
ly to an adjective, you must use
"In a sillier manner" ->
"In the silliest manner" ->
If an adverb is the same as the adjective form, you can make a superlative using
"In a faster manner" ->
faster (ex. "He ran faster")
"In the fastest manner" ->
fastest (ex. "He ran fastest")
sillilily, this is entirely nonsense. The reason is that our
ly rule only applies to adjectives. You can not apply
ly to an adverb and expect a "double adverb". An attempt to apply the rule directly would result in:
"In a sillily manner"
Notice that since
manner is a noun, it should not have an adverb describing it. In your examples the word "suggesting" came out of nowhere. Nothing in the grammatical construction implied that there was suggestion.
In the case of
sillililiest we encounter both of the above problems simultaneously. First, you attempted to make an adverb from an adverb by adding
Then you attempted to apply
er to make a superlative
Both of these can not be done. The first because
ly only applies to adjectives, not adverbs. The second because to make a superlative from an adverb which was formed by adding
ly, you must use 'more' or 'most'. Again- you introduced the word "suggesting" which came out of nowhere.