Place the TT so the awning is downhill. If you're on a slope the trailer cabin will be level, but your awning will tend to follow the slope of the ground. This doesn't look showroom neat but it's perfectly stable and watertight. What you don't want though is a dip in the ridgeline at the cabin, because water can pool there. It's better for the ridgline to be hog-backed.
Don't take the jockey wheel off unless you really want to or have to while travelling. I only take it off for really long trips.
You need the jockey wheel to level and support the trailer when on the pitch so definately don't take it off then!
You don't want to put the steadies down so far that they lift the trailer off the main wheels. Steadies are for steadying, not jacking the trailer up in the air. Main weight should still be on the axle and jockey wheel. You want positive contact with the ground though at the steadies, not them dangling an inch above the earth.
Take a cheap spirit level to help with levelling the TT. Level front to back using the jockey wheel. Try to have the TT on a reasonably even surface side to side....huge variations need a ramp under one wheel but that's usually unnecessary on classic TTs where the wheels are pretty close together.
Chock the wheels at this point, once the trailer is level and before you unfold the canvas.
It's much easier to unfold and do the poles on the cabin if two folk do it, one at the drawbar end, one at the step end. Work symmetrically. It's esier to work round and put extend poles half way, then go round again and do them fully rather than shove everything out on one side before starting at the other. I always have the drawbar end btw. I'm shorter than hubby so it helps to stand on the drawbar sometimes.
If poles are sticking, give them a tiny squoosh of aerosol Fabsil. NOT grease, WD40, Vaseline or anything else that can damage canvas. Wipe off excess Fabsil.
Take spare rubbers, guylines,pegs. Two mallets go faster than one. Take pads for under the steadies and for the bed legs.
Make sure the beds are level, both ways. Sleeping on a slope is annoying.,
The easiest time to hang the undertents is before you drop the cabin canvas. If it's raining though get the cabin canvas down quickly and do the undertents by crawling in later.
When you peg out the cabin canvas ensure a good gap from the bed boards at the back, back corners and sides. Front doesn't matter if you're using the awning. I get inside and check the gap while hubby pegs. Use the waist guys too if you have them. You don't want the canvas knocking into the bed boards and springing a leak.
Don't let dogs or children in the cabin area till it's levelled, unfolded and pretty well nailed down. Poles can slip, canvas can get tugged unexpectedly and ripped. Once you have the four corner pegs in it's safe.
You can do the awning by putting the poles up at half hight as you say, or by fully assembling the frame then pulling the awning canvas over then. Your choice. A lot depends on how tall you are.
The time and place you're most likely to rip the awning canvas is pulling it over the front of the frame, on the sockets for the stub canopy poles. Get it right over the frame here, sockets through the awning holes and fit the stub canopy poles then, even if they're not tidy or exactly set. This will protect the canvas. Every third TT canvas on ebay seems to be torn here. Don't join them!
Give yourself two clear hours to put it up the whole thing. You'll get this down to nearer one hour with practice but you don't want to stress yourself by rushing the first time. Slow and steady. Oh, and take the instructions!!!!
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Topic: planning our first trip out- tips please
) Can't offer much advice though - we took coloured tape to make sure poles were color coded and I made a list of any replacement parts we would need. They have now arrived so this time I will be able to replace perished rubbers and dodgy frame springs and buttons. Someone did suggest a spirit level and we didn't use one - but I will do next time! Awful sleeping on even a slight slope! Our bed legs slid of the wooden plinths in the night - woke us with a jump, so am going to try the trick of screwing jam jar lids to the plinths. I also got some proper groundsheet pegs - need to make sure we are windproof! We will be taking our two spaniels - dog cage is a must! And am planning on tying them to the towbar rather than a ground spike as they will probably pull a spike out! 
Cheers! xx
. We have carpeted Tessie this week; filled her storage boxes up with bits and bobs; and finally had a go at putting the awning frame up. When we bought the TT, it didn't come with any instructions- just a diagram of the awning. Luckily the poles had been colour coded by the previous owner. It took only about 15 minutes (didn't manage to put the full awning up as it started to rain), but at least we have a better idea of what to do 
. I doubt that we will put the sun canopy up on this trip, but you never know!
