I think that your XP will be fine when you start TOB. If not, it should not be a major problem as you can use Shadowcheater or CLUAConsole to bump it back up - as long as it is under 8 million you will be OK.
You take any items you are carrying with you, and you are usually given a few more too.
I don't know the romance answer, but I couldn't leave you sitting here with no answers after your heartfelt plea in Gen Discussions!
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Time is an illusion. Lunchtime doubly so.
Epona of The Laughing Hyenas