Ok...so for the purposes of licensing there is a difference between the line of demarcation...or what we might call Colregs. And the boundary line.
The Colregs line is where the inland rules end and where international rules apply.
The " Boundary line " is a different line see attached
link.Grossetti License Consulting
If you sail out of Long Island sound to go to Block island you will cross colregs, but not the boundary line.
A Near Coastal Endorsement to a OUPV license requires 90 days of service beyond the " Boundary line" served any time...(uninspected vessels)
In addition to the other license requirements..you need a total of 360 days service...(1 year)
90 of those days must have recency...( last 3 years)
So to answer your question, none of the waters you mention count as beyond the boundary line but you can still obtain an OUPV inland and then upgrade when you are able to document near coastal time. You can also upgrade to Master Inland, get a towing endorsement, and a sail endorsement, and a Near Coastal Endorsement to a Masters License.
Tonnage is another discussion.
Hope this helps.