<prompt> Human: So I guess im technically homeless becase I have been living in my car for the last month, but I just cant afford a place to stay while Ive been saving up for the deposit on a new apt. I have been very into vintage watches for many years. Never really had enough money for something nice. I saw some eatate sale signs the other day and thought Id check it out for fun. I discovered that there were a bunch of really old beat up Rolex watches there. I recognized that they were pretty valuable. I know it wasnt the smartest thing of me, but I took the 3500 I had saved for my new apt and bought the 4 watches. I took them too a really awesome local vintage watch buyerseller in my area to see what I could sell them for. Two of the watches are what are known as paul newman daytobas. I knew when I had first bought them that they were very valuable, but it turns out that one of them is worth around 350k and the other one usually sells for around a million at auction. The other 2 were old submariner watches that the guy offered me 25k for both. I took the 25k, as I desperately need the money, and I still have the other two. The owner offered to represent me at a christies auctionfor and thinks they should go for a total of over a million for both. I havent given an answer and thought Id come here for help. I really dont know what to do. First off, the 25k is a TON of money for me. I am using part of it to pay some bills and get an apt. What is a good thing to do with the rest? The guy is very respected as an honest vintage watch seller and I think I should agree to his deal. He wants to get the watches serviced by a really great old watch guy Bob Ridley, and then auction them off. Is this a good idea, and what in the world should I do with the money after the auction? Do they give me a big check? Taxes? I really dint know.  <response>: 1 Open a safety deposit box TODAY and put the watches in there.2 Dont agree to the auction yet. You need a lot more info before making a decision of this size. I think if you own it for a year before selling you will qualify for long term capital gains. But you should check this with an accountant. This could save you over 100,000 in taxes3 Do you live in a high income tax state? If so, you should move to a no income tax state Alaska, Florida, Nevada, South Dakota, Texas, Washington, Wyoming before selling. This could also save you over 100,000 in taxes. If this is the case, do NOT rent an apartment yet... take some of the 25,000 you got for the first two watches and check in to a cheap motel or a hostel until you know what your long term plan is.4 Make sure you get opinions from 2 or 3 more professional watch collectors before making a decision on how to proceed. 