Howdy fellow bikers Just found your group on the net while researching sport touring motorcycles, bravo to the members I am impressed with the genuine conveyance of information without the flaming and typical member bashing found within other forums.
Welcome. I'll try and answer what I can.
How overloaded can you ride an ST1300 on a regular bases. I am 260, wife is 190, then add the full side bags heavy leather jackets etc. I’m guessing 530 lbs of load on the bike for the commute. The bike with fuel is approx 720, so that’s 1250 lbs. man are we fat or what. So is anyone in the group running this heavy and what are the consequences?
Anywhere near max GVW and the handling is going to get crappy. You'll be at the max preload on the rear shock and the front travel will be greatly reduced. Aftermarket front springs, I run Sonic's, and a new rear shock will help some.
Also what is the GVW in the manual?
401 lbs for a US spec bike and 410 for a Canadian........ The bikes are identical and I have no idea why the difference.
How prevalent is the high speed wobble, is this a common issue or a rare anomaly. And at what speed is this likely to show up?
I've had it happen on two different bikes. The only common elements were a top box and speed. Both times the wobble started at about 110 mph. In one instance changing the screen position on the fly cured it immediately, in the other nothing helped. OK slowing down did but that shouldn't count.
How about loading / overloading affecting the wobble?
Possible. The majority of riders never experience it. Many will proclaim that it's not an issue as they've never had it happen. It happens, not often and not at sane speeds, but it happens. Anyone who says different has their head in the sand.
My V-star with a tall windshield still buffets my head anyone with this problem on an ST?
The stock screen is a compromise between performance (wind drag) looks and protection. There are many aftermarket shields out there. I find wind noise a bigger problem than buffeting so I always wear ear protection.
What is the top list of options you have added to your bike?
PIAA 910's on Dick Seng mounts, Starcom Advance, Sargent Saddle, Garmin 276C, Valentine V1, Givi 52 ltr. top box, Clearview GT small screen in the spring/fall, upgraded horn, BMW style and standard cig power receptacles. The PIAA's, Garmin and V1 are the most important.

As an owner of a ST1300 if you were buying a used ST1300 what things would you look for and what questions would you ask the seller?
If it's an '03 or '04 there were a few recalls that should have been done. One for a wire loom routing issue, the other was an inspection of the linked brake proportioning valve.
Any particular year have updates that make it more favorable as a used purchase over previous model years?
The '03 Std. model did not have an adjustable windscreen, after that they all did. There were a few heat shields added to the post '03 models and there appears to be a yet to be determined (cosmetic or functional) addition of some small body panels on the '08. Other than that the bikes are identical.
Thanks in advance for your quality advice.

You're welcome..... hope it helped.
Edited to add:
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ST Owners if you want a whole bunch of answers.