It honestly didn't take me long to shell out the mulah for shiny things. Twenty bucks in Second Life can stretch a lot longer than almost anywhere else, including Gaia Online and Facebook. Pick the right stores and you're looking at a lot of outfits. My main focus was always clothing, though. To purchase land, either on an estate or on the mainland, you have to shell out regular money, and when I started paying for things it was very much ad hoc and in response to how much I thought I had in the bank.
My first home was on the land of a friend I met through philosophy discussions. We all had little sections, and our mismatched builds clashed gloriously with each other. I did some of my first building there - my ball houses, which have never made it out of my inventory. That land went after a while - land is expensive in Second Life - and I moved into the sky over a Sim I used to regularly go to discussions at. Sadly, these days most of the discussions are at 4am, far outside of any time I could join in, but in many ways I had moved on.
Then I was invited for a while to live with some other friends, but as time passed I felt less and less welcome. It became painful to log in there, to look around and see evidence of a person who now couldn't be bothered to say hello to me but could make comments on a blog about me and pretend he was brave enough to say it to my face (and who could then lie to my face about it being about me despite repeating almost verbatim things that were said in that post). I moved out when it hurt too much, and all evidence points to me never being missed so I can't say I much regret it - but I did regret losing the feeling that I had a home and people who cared if I was around.
A few days ago, as an early birthday present to myself, I splurged and finally took a step I'd been considering for a while - becoming a Premium Member and claiming my Linden home for my own. I chose the elfy lands, a cute little cottage with a generous porch and a room I could make into my dressing room. I was given lovely housewarming gifts - a bunny and two horses - and had the fun of not only decorating it as I wished, but knowing this was my space to invite other people into; my home even when people no longer want me around.
( More pictures of my home here. )