How to know when's the right time to sell

[Justin Ashworth]

I've really been enjoying BP - from podcasts to blog to forum, it's been extremely valuable. This is my first post to the forum so go easy on me. :-)

I have a question about a rental property which used to be my primary home. Currently, it's worth about $360k (Zestimate, which seems fair).  I have 10 years left on a 15 year mortgage at 3.5%. Rent is a market-reasonable $1995/mo and it's been vacant for just 1 month (due to breached lease) out of the last 8 years and 5 tenants. I self-manage and because of the aggressive 15 year mortgage I take home just $450/mo which just goes into a savings account, so I don't split out repairs and vacancy. I have tenants committed through next June.

So the question I'm wrestling with is....do I sell to pull my equity and buy many more cheaper properties, which I'd likely have managed for me and would likely be out of my area (near Portland) due to housing costs? This 2003 house is a fairly low-maintenance property and I realize that to buy other properties I'd likely be getting into more older properties which inevitably will require more maintenance. Or, perhaps it would be better to refi for a longer term to have more take-home?

Any help appreciated for this newbie investor.

Thanks!

Justin