Good thread!, I have read in in one huge read, so am a little shellshocked, plus I have not played Traveller in years, PLayed some New Era a long time ago; that being said though.
A colonization effort could well be started and funded by a government for defensive/strategic reasons. Get a system going, load it up with loyal folks, create a tax base, get money from asteroid mining/lanthunum etc. Start your own Pocket Empire.
When picking what you need, I think you have to look at what you want to start with, and maintain. If I had to 'take on' and build a colony, I would want to bootstrap it as fast as possible. So my upfront cost would be bigger, but the return on investment time would be faster.
Someone mentioned asteroid mining. What if you took in a smelter in a ship, (and one of those gasgiant processing ships that was written up years ago (anyone remember those? if so, can you post where it is?)) Asteroid mining provides fast access to metals.
I would take a computer controlled machining system, so I could make parts out of slabs of metal.
I would want enough piping (or a pipemaking machine) to set up a refinery for plastics.
And stealing ideas from Zubrin (whose 'twaddle' ideas of living off the land is now the plan for Mars, using local resources.
Thermal depolymerization technology provides oil, and lubricants from biomass. This can give me plastic as well.
Solar Bubbles and a microwave reciever provides free energy (Marshall Savages Colonize the Galaxy in 8 Easy steps)
So we have power, metal and plastic. We can now make Gameboys, or electronic transmissions. Or DVD readers to play the educational discs we brought along.
For power on the ground, Use the plastic to make pipes, bring along a diving crew and make an OTEC (Ocean Thermal Energy COnverter). This needs a water world, but we did say Earth like world in our list of many assumptions. This provides fresh water, salt water for aquaculture, electricity.
Steal again from Savage and you get sea-crete buildings...
Heck, ground a small ship with a power output in teh Megawatts and you can grow buildings with rebar made from meteoric iron.
Upfront costs, Billions of credits, but you bring with you the technology and equipment to build the infrastructure that you need to bootstrap yourself up the tech ladder.
Zubrin had an equation where he ends up with ethylene, plastic. Thermosetting plastic was mentioned before. Take a plastic desgin factory, tons of machinery, but you can make anything out of plastic.
IMTU I had the Fullerites setting up colonies. Geodesic domes and Dymaxion houses. All self contained units. All Praise Bucky!
Self sustaining? depends on how you measure it. Take a skimmer and a plastics plant and you have greenhouses. Free heat from fusion plant, plastic boxes with compost and earth and you have growboxes. Plastic mulch covers no weeds.
www.earthbox.com has a patented plastioc box that cuts water use. I called them a few years ago, they did an acre of these little boxes, thousands of them. no weeds. A lot of plastic, but no weeds.
So now you have a tech reliant system. You better start mining surveys for aluminum, gold and all the other stuff you need. Asteroids might be fastest (you have ships after all)
Again, the point is to take the items with you that will sustain your tech level as you want it. You won;t be able to repair everything yourself until you find the raw materials to use your machines to make the tools to repair things, but you know how (take along the contents of the Universal Patent office) Every instructional video ever shot, and your colonists are repairguys and engineers. Go Scotty!