Note: All group matches will end in a result (Extra time and penalties if necessary) to avoid any issues about tiebreakers during this stage. No news on whether wins after extra time and penalties will also be worth 3 points. It is also not clear whether this applies only to Round 2 (it is mentioned after the Round 2 groupings and also the "5th place playoff group" in the official release). Also, the release says that teams will be ordered from Round 1 based on points (but then the 2nd round groupings contain things like "7th best runner-up". If the 1st round is based on points, it's possible that a 3rd placed team in one group (with 2 draws) could finish with more points than a 2nd-placed team in another group (with 1 draw and 1 defeat). Even if extra time and penalties decide these matches, it's still possible that a 3rd placed team in one group could finish with a better record than a 2nd placed team in another group.
On a less complex note - nice to see the long-awaited return of Sint Maarten.
Some other issues:
In the 2nd round groups:
Saint Vincent & the Grenadines enter here
1st best, 2nd best, 3rd best, 4th best, 5th best, 6th best, 7th best Group Runners-up from Round 1
1st best, 2nd best, 3rd best, 4th best, 5th best Group Winners from Round 1 - "6th best Group Winner from Round 1" and "7th best Group Winner from Round 1" are missing. Instead there are "Best remaining team from Round 1" and "2nd best remaining team from Round 1". Can't work this out...
In the 3rd round groups:
Jamaica, Haiti and Trinidad & Tobago enter here
1st best, 2nd best, 3rd best, 4th best Group Runners-up from Round 2
1st best, 2nd best, 3rd best, 4th best Group Winners from Round 2
"Best ranked team from Round 2" - Not sure what this is supposed to be. 5th best Group Winners are missing (there are 5 groups in Round 2).
This link doesn't help clarify: https://en.m.wikipedia.org/wiki/2017_Caribbean_Cup_qualification
It suggests that the Top 4 group winners and top 4 runners-up advance, along with the best 3rd-placed team. This suggests that the 5th best Group Winner does not advance. This is clearly wrong. How can a 3rd-placed team qualify and a group winner be eliminated? Nonsense.
In the "5th place play-off"
The 3 best 3rd placed finishers in Round 3 (why is this called the "5th" place play-off? These teams would be placed 9th, 10th and 11th in Round 3 qualifying. It should clearly be "best 2nd placed finishers". The Winners of each group (4 teams) will qualify for the final tournament. The 5th, 6th and 7th placed teams will play-off for a spot in the CFU-UNCAF play-off for entry into the CONCACAF Gold Cup.
There are only 25 teams in qualifying, even though the release says 26 teams will take part. Missing teams are Bahamas, Bonaire, Cayman Islands, Montserrat, Saint Lucia, Turks & Caicos Islands.
Finals in May 2017 (not been decided where yet)
All in all, a confusing press release. Maybe I'm nit-picking, but these types of things don't help.