Towing with a 2021 tundra 1794 and looking at a 08 w warrior superlite fs2300. Too heavy? Thoughts?

IT will boil down to "Do you have the payload!" 

My case, 900 lbs plus 1200 for family of 6, a couple of malamutes at 150 ea, rack on truck, canoe on rack, a few bikes for kiddo's, generator......we needed a 1 ton to pull a trailer with twin 3500 lbs axle, or a max total gvwr of 7000 plus 1000 max lbs of hitch = 8000 total. We in reality needed 3000 lbs of payload. Yes you truck, my 2014 GM 1500 is rated to tow said trailer, but with 2000 lbs of payload, not going to happen! I would be legal on GVW if I bought enough GVW/GCW tonnage, but depending upon the where I am traveling, not safe! I could do the trailer now with current truck, no kids etc. #2 sone bought a 6500 gvwr trailer to tow with his GM1500 recently.....
Reality, both yes and no and somewhere in the middle is the correct answers, ie there is no correct answer. Yes it is a math question to figure out if you are safe and doable. 

Marty