Learn English – originate + from / with / in / as

The Old English word lang has suffix forms -ling and -long, (“with the direction, duration, or length”), similar to -lic (“with the body or form”) that survives as the very common -ly adverbial suffix form.

The -ling form, once used in words like hinderling (“in the backward direction”) has been supplanted by another usage, the nominal diminutive: darling, yearling. The -long form still survives, with all three senses, in words like headlong, nightlong, and footlong.

The suffix is adverbial in directional modifiers like headlong and arselong, adjectival in metric modifiers like footlong and nightlong. When combined with a quantifier to form an adjectival or adverbial phrase, the metrics compounds break into their component words:

• I ate a footlong sandwich. [adjective]
• This sandwich is one foot long. [adjectival phrase]
• This sandwich measures one foot long. [adverbial phrase]
• We attended a nightlong party. [adjective]
• We stayed at the party the whole night long. [adverbial phrase]

As these express spatial and temporal dimension rather than relationship, it's not clear whether these are adpositions or simply adjectives with an idiomatic phrase order. However, the close similarity to a hole one foot through or party the whole night through suggests that they may indeed be postpositions.

While RHK Webster's lists the above usage of 'with' as a prepositional one, it flags the peculiar usage, calling it a 'function word'. Though this is rather misleading (all prepositions lie somewhere along the lexical word --- function word continuum, their actual location dependent on the actual context they're used in), RHKW are right to imply that this is a very marginal use even for a preposition. They don't even attempt to give a definition of this sense of 'with' other than an explanation of the use to which it is put in a context:

(17.) (used as a function word to specify [introduce] an additional circumstance or condition): We climbed the hill, with Jeff following behind.

It is almost always more idiomatic to drop the 'with' and use the remaining absolute construction. The RHKW example is unusual in that the inclusion of the 'with' sounds slightly more natural, if anything; this is probably due to the lack of semantic cohesion between the main clause and the absolute clause. Two sentences would (unless previous context linked the clauses more closely) be equally appropriate, with little change even in emphasis: We climbed the hill. Jeff followed behind. Of course, stylistically, this is more staccato.