To be honest, having a really high piloting skill is not as good as you may think. Yes it will decrease travel times, but not by that large an amount, and does decrease chances of being killed when aborting hyper, but not many people do that if they can help it. Unless you are trying to max it out for combat or something, 3 would be a reasonable max for piloting as much more than that uses up valuable skill points for not that much gain.
Looks like you want a character that has a trading bent with usefulness for prospecting and mining/construction/production. If you are basing your skill choices due to rules effects rather than RP aspects, best to go with the trade 5 option. Used fo FI, and with the number of Trade 5 people running around to get max income, anything less is not much good. If its an RP aspect, then by all means ignore the above. And you can always spend your first 8 skill points to bump it up to 5 if you so wish at that time.
Again, as above, Leadership is useful for reducing times for the linked activities, but going above 3 may not provide returns on your skill points when you could use them on a couple of other skills. Granted we say specialise rather than generalise, but personally I don't see much worth in going beyond unless you have plans to be uber - I don't believe the difference in times is that much that it would make a huge different in 99% of cases.
Comp Ops is the exception to the above - you will want this as high as possible for prospecting. Due to the way it works, the higher your skill, the better chances you have at finding something, and the difference can be noticable. This would definetely be one of the skills I would suggest maxing out if you are heading in that direction, like Trade.
So, going with all that, your first choice of a Hutt with Trade 5 etc would seem to be the best. Should still be able to fly a capital, use groundhogs if you end up prospecting, and do most things. I would expect most factions would have a capital handy they could let you use, more so the larger factions and govs as they would have more assets to look through.