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So how about this scenario? I'm 54 years old with 15 year old twin boys. I work as an outside sales representative with great job flexibility and live in the Seattle area. Because of the extensive travel I've done throughout my career, I'm a lifetime Platinum member with Marriott. For the past 10+ years, I make a point of going to Hawaii at least once a year, sometimes twice. While I would never purchase a timeshare directly from Marriott, I'm strongly considering purchase one week directly from a seller on Redweek. Why? Because I want the flexibility of being able to select the week I travel every year. Yes, I can always rent someone's TS, and I have with great success, but it's more costly and challenging to find the exact week I want. For the properties I'm looking at, I can purchase a 2 bed / 2 bath oceanfront at a Marriott (or Westin) property on Oahu or Maui for $8-12K with annual dues of $2,300 or so. Without question, I'll never be able to make back the down payment, but given my frequency of usage, I'll be able to chip away at the number if I can save $500-$1000/week each year by not renting someone else's timeshare. Hawaii is a different destination than lower 48 properties, as owners don't typically rent their weeks for less than $3500. I'm still not ready to pull the trigger, but it's tempting me. Your opinions are appreciated.