Howdy, Thesedays! I'm in Florida, too!
Here in Fl (like most states) the CRTP is 7-7.75 years from date of final delinquency.
The "reporting date" means, AFAIK, the date the CA updated/reported the account to the CRAs.
"Date assigned" is the date the collections agency either bought the account or was assigned the account by the original creditor.
Most important in your situation (IMO) is the SoL. Here in FL, for medical bills, it's 5 years (4 years for open/revolving accounts like credit cards). Though sometimes, I've heard that medical bills fall under the 4 year "catch all" SoL.
Being out of SoL gives you leverage in dealing with the CAs. Since they can't legally sue you (they CAN sue, but if you appear in court -- and you MUST or they'll win by default -- they'll lose due to SoL being expired. Essentially, the court tells them that they've lost their "bite at the apple.") the only way they'll get their $$ is if they agree to allow you to pay for deletion of the tradeline.
SoL is determined by the date of last activity. So if you defaulted on the debt in 2/02 it would be out of SoL in 2/06. HOWEVER, if you made a payment, say, in 3/05, that would reset the SoL clock and the SoL wouldn't expire until 3/09.
DID you make a payment on the first collection (the one for $60)?? That's what it's looking like ... in that case, with that one, you're still in SoL, so they can still sue you. Ditto with the $52. It looks like the SoL has expired on the $399 one, though.
As to how to handle it, I'm mot well versed in the whole HIPPA thing. Ilecs is awesome on that topic, as is SideWinder. Hopefully, they'll wander in and chime in on the topic.
I THINK though, that you can DV the oldest (the $399) on the off chance that the CA won't be able to validate due to it's being so old. If they can't validate, they have to remove the TL with the CRAs.
With the others, I wouldn't offer a PFD right off the bat because you have no leverage in "forcing" them to accept it (since they can still sue -- they have nothing to gain, really, from allowing you to PFD). Again, hopefully, SW or Ilecs will chime in. Listen to them -- they are the BEST!! Ivyalmighty might wander in, too. She's a butt-kicker, too!!