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Other posts I have read make it sound like you start with some sort of default house and can upgrade later.
Correct. Your first home will be an Inn room in your starting village. It's free to purchase and costs 5 silver a week in upkeep. You can upgrade to 2, 3 or 5 room housing. Bigger housing gives you more slots for selling and storage.
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Do all upgrades require guild membership?
No, but the purchase price and maintenance cost you more coin. If you're in a guild you pay roughly half the coin cost of the identical non-guild house, plus status (which you get for doing writs, quests and various other tasks). Same deal with maintenance. You can buy or quest for status cost reducing housing items.
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What happens to your things when you buy a new house? Do they automatically move?
No. I'm pretty sure you have to empty your house before you relinquish it or you lose everything in it. There's a handy button that lets you pick up eveything in your house (as much as you have inventory slots for, at least). It's still a PITA getting 100's of items out of house 1 and stored somewhere like your bank and your person then get them to house 2 :P. I've heard conflicting information on whether your storage vault boxes transfer automatically. If someone knows, please enlighten us :) If they do things would be somewhat easier.
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What is the advantage to having a new and bigger house, or is it just for status?
Bigger housing gives you more slots for broker selling and storage. You can also display more stuff in them, 100 items per room.
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Where are these houses, especially the starter house it sounds like I should have when I get to the mainland?
Look for the Inn in your starter village, with the bed icon, and hail the housing NPC. The bigger houses are in the main city zones.