I hear you and see where you are coming from. There can be a blurry line between investment and gamble. When you start using words like hope and emotion I think you start skewing toward gamble and away from investment. At least that’s how I look at it. Sure, thinking about potential future value of any large purchase should be part of any significant financial outlay. When I make a larger purchase, I am making an assumption that I will recoup some of my investment if I should decide to sell but I am also OK with taking a loss if that should be the case. The emotional gain of the art can translate to a financial loss and this is a balancing act I accept. Does this play out very often? So far, no (at least in what the market tells me my art is worth vs what I paid) but I have only held my art and not sold. Who knows that the future holds? That said, I view this exclusively as a hobby which helps to shape my view on purchases. I know a lot of people look at a lot of their purchases and are able to buy low and sell high (on average, across the board) and use this to fund purchases that are more emotionally based. For those who can do that, I applaud them. For me, I’d rather just buy for enjoyment. All approaches are good in my book! $.02
gam·ble
1. play games of chance for money; bet.
2. take risky action in the hope of a desired result.
in·vest·ment
1. the action or process of investing money for profit or material result.