A few things are proscribed or regulated by law (or the implementing 'federal regulation') on the basis of content -- e.g. 'advertising'.
Other things are proscribed/regulated on the basis of the methodology/technology used. e.g. autodialers, pre-recorded voice announcement, etc.
The regulations on 'advertising' *do* provide an explicit definition of what is, and is not, covered. And there has to be a direct relation to a solicitation for "the purchase or sale of property, goods, or services."
By 47 USC 227, and the FCC rules implementing it,
Dialing (1) 'emergency numbers', (2) _patient/_guest_ rooms at hospitals, etc., and (3) 'paging service', 'cell phone', 'mobile phone', 'radio common carrier', and any other 'called party pays' service is forbidden.
Dialing 'staff' numbers at a hospital, etc. is _not_ proscribed by law.
The *ONLY* restriction on dialing 'large PBXes' is that they may not tie up two (or more) lines simultaneously.
All of the above apply *ONLY* to the use of autodialers or 'pre-recorded' voice announcements.
And, they apply *regardless* of the content of the message being delivered.
The only explicit mention of 'advertising' as a proscribed activity is with regard to the sending of unsolicited FAX messages.
If he only called -one- number of your business at a time, his calling was legal. Business numbers, not subject to the DNC list; not 'called party pays'; and not an 'emergency' line; Q.E.D.
The statute, and the various sections of the CFR implementing it, is quite specific.
"(3) The term "telephone solicitation" means the initiation of a telephone call or message for the purpose of encouraging the purchase or rental of, or investment in, property, goods, or services, which is transmitted to any person, but the term does not include ..."
If the call is _not_ "for the purpose of" getting some one to purchase or rent "property,goods, or services", then it is not subject to restriction.
The FCC _did_ exempt, by rule, unsolicited calls that are "not of a commercial nature".
The 'other' regulator, the FTC, is by statute, restricted to regulation of 'commercial' activities, and *their* telephone regulations apply ONLY to calls related to the offering for sale, or soliciting the purchase of, 'property, goods, or services'. _They_ have held that calls just 'setting appointments' for someone to make an actual sales pitch, are covered by FTC regs.
The 'happy holidays' call _is_ probably legal, in a strict interpretation of the law. OTOH, the dealership may well be doing more damage to it's reputation by making the calls, than the goodwill it generates.
The free ring cleaning offer is also probably, technically, non-commercial, and thus exempt from the telemarketing restrictions. A great deal depends on exactly how the message reads -- if they mention only the free ring cleaning, who they are, and when they're open, they're almost assuredly on 'safe ground' legally. OTOH, if they talk up _other_ things they do as well, -- .e.g, " free ring cleaning offered by XYK jewelers, purveyors of fine diamond jewelry, and quality watches. Distributors for Omega,Wittenhaur, Rolex, and Movado watches", _that_ is likely to run afoul of the FTC telemarketing rules.