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Congratulations on your new purchase. Got a good deal it sounds like.
1) You do not need a CDL to pull a trailer.
2) Check your Tahoe manual to see its tow ratings. Same with any conversion van you consider.
3) A generator is good if you really need it. Most are noisy, so choose wisely based on where you will camp. You will not have a good time with others looking at you with a "hairy eyeball".
Hope this starts you on the road to help.
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