Take the equity or reinvest?

[Jeremy Clarke]

I've done some buy and hold investing the past 5 years or so. I've had the benefit of the market on my side so the 3 properties i've owned have appreciated nicely since then. I sold one, live in one currently, and still own one investment property. I'm thinking of selling the investment property and taking the equity later this Fall.

If i sold this property i'd keep the one i live in but have a nice chunk of change to reinvest somewhere (likely the midwest). If i go this route, my math tells me i can make close to enough to live on and work optionally if i rent out my current house, so that would free me up to travel and such.

I'm 30 years old and don't want to work my whole life, but i also don't want to be bored. I don't think i'd bring in enough to truly "retire" (health insurance etc). Any advice (maybe some of you with more life experience than me), would you take the equity while it is there or would you hold the property that has been appreciating very nicely year over year?