Josh, lets start with the estimated loaded trailer weight.
You have listed an Unloaded Weight of 5910#. I believe that value is from a brochure or website and might not reflect the actual UVW of a typically equipped 284BHSL.
This
Holman Motors, Inc. web page shows the actual weight stickers for a 2014 284BHSL on their lot. Image 26/28 shows a UVW of 5958 and image 28/28 shows a maximum allowable cargo of 1642#. The list of Upgraded Options includes just about every available option.
I think it is very reasonable to assume a UVW of 6000# to use as a basis for estimating the loaded GVW of any 284BHSL you might find. Then, it's up to you to decide how much of the 1600# CCC you might use.
First, let's work through the numbers using a TT loaded weight of 7000# (1000# of cargo). Since you plan to use a ProPride hitch, you should add approximately half its weight to the weigh of the TT.
Then a realistic tongue weight would be 13% of 7100# = about 900#. The PP hitch would allow you to get by with even a lower TW%, but I recommend you use 13% for estimating purposes.
Since the PP is a weight distributing hitch, you can assume that a load equal to approximately 20% of tongue weight will be transferred to the TT's axles -- leaving a load of about 80% of 900 = 720# to be carried by the TT.
The other half of the PP's weight will be carried directly by the TV giving a total of 720+100 = about 820# to be carried by the TV.
Adding your estimated 680# for people, truck cap, and "other" gives a total of 820+680 = about 1500# total TV cargo versus your max payload number of 1752# -- a margin of about 252#.
For comparison, if you were to load the TT to its 7600# GVWR, the above process would give a tongue weight of about 0.13*7600 = about 1000#.
The load induced on the TV by the TT plus hitch would be about 0.8*1000 + 100 = about 900#. Adding 680# for people, truck cap, and "other" gives a total TV cargo of 1780# versus your max payload number of 1752#.
Again, only you can know how much of the TT's 1600# CCC might be used.
BTW, the assumption of 20% load transfer to the TT's axles assumes the WDH is adjusted to achieve 100% Front Axle Load Restoration versus the 50% FALR specified by Ford.
If you were to opt for 50% FALR, the load transferred to the TT's axles would be equal to about 10% of TW.
Ron