Council of Elrond

Say I have Barliman and Robin, untapped, in a company at Bree during the site phase. I tap Robin and Bree to play Mistress Lobelia. Two related questions:

(1) Can I now tap Mistress Lobelia to get a Noble Hound from sideboard, and then tap Barliman to play the Hound on this same turn? (As a follow-up question, if this would work and if I had 2 additional untapped characters at Bree, would this allow me to play 2 "free" minor items this turn, one for each ally I've played?)

(2) Could I instead tap Mistress Lobelia to get a minor item from my sideboard, say a Healing Herbs, to play as my "free" minor item on Barliman?

Kjeld wrote:[...]I tap Robin and Bree to play Mistress Lobelia.[...]

Bree taps after successful playing of Mistress Lobelia; Bree is not tapped to play Mistress Lobelia.

Kjeld wrote:Can I now tap Mistress Lobelia to get a Noble Hound from sideboard, [...]

Mistress Lobelia cannot tap to get anything from sideboard; may tap to search for resource (and get it to hand) in play deck, or in discard pile.

Kjeld wrote:[...] and then tap Barliman to play the Hound on this same turn?

Noble Hound may be played under control of Barliman after playing Mistress Lobelia and tapping it for any reason, in the same site phase.

Kjeld wrote:(As a follow-up question, if this would work and if I had 2 additional untapped characters at Bree, would this allow me to play 2 "free" minor items this turn, one for each ally I've played?)

No.

CRF, Rulings by Term, Items wrote:The "free" minor item may only be played immediately after playing the resource that
taps that site.

(One) "free" minor item could be played after playing of Mistress Lobelia. Playing a resource at already tapped site does not tap the site.

Kjeld wrote:(2) Could I instead tap Mistress Lobelia to get a minor item from my sideboard, say a Healing Herbs, to play as my "free" minor item on Barliman?

No. For many reasons.
Not "from sideboard".
If the copy of Bree in question is hero version, then minor item is not playable there (minor item may be played immediately after playing the resource that taps that site, but "may be played" does not imply "is playable", nor vice versa).
Even if the copy of Bree in question is minion (with Double-Dealing, so we are speaking about Fallen Wizard company), where minor items are playable, a "free" minor item may only be played immediately after playing the resource that taps that site. Tapping Mistress Lobelia after playing it causes that any next action will not happen "immediately after playing the resource that taps that site".