Re: Help what sail to raise 1st?
Not sure about on a masthead rig, but on a fractional rig you can do some considerable damage if sailing with just the jib depending on your rig setup. It all has to do with rig tension.
For a dinghy, especially an FJ or 420 jib up first so that you can tension the jib wire which will pull the mast forward. On some larger dinghies this is unnecessary when the jib wire tension can be adjusted on the fly.
Unlike everything else on a small boat the higher the wind the looser you want the jib wire because it will give more mast rake (mast angled backwards). This is especially beneficial downwind. In lighter air you want the mast farther forward (less rake will result in more power). If you want to really crank the *@$&$ then get someone to pull on the forestay while you push the mast forward with you foot and cleat off the halyard. As you go it is easier to let out the tension than to add it. If you must tension the jib wire while you are sailing, head dead downwind so that the mast is being pushed forward and use your feet to push it forward while cleating off the halyard.
On a larger boat or a dinghy with adjustable jib wire, main up first, then jib.
Downwind spinnaker up, jib down. Then jib up, spinnaker down.
This is probably more than you wanted to hear, but hopefully it helps.