To Sell or Hold?

[Rodney Smith]

So I will try to be brief, but in short my wife and I bought a 4 plex about 3 years ago (read more detail here - http://www.biggerpockets.com/forums/223/topics/139...) .... So we initially bought this with a short term strategy in mind to stabilize financially to make a career change. As we've learned more about REI we've decided want to do more and need to transition into a longer-term strategy.

So we have a 4-plex that we owe roughly $150k on and I am still researching this, but I think we could make a case for asking roughly $300-$330k. I am thinking that I would be smart to take my gains and either re-invest them into a better long term market (currently in Redding, CA). Also, the goal of the 4-plex was to stabilize income to transition into a new career, which I could now easily do from the amount of appreciation I could realize by selling now.

I don't want to make the mistake of getting greedy and missing out on a good time to sell only to see the market take a pullback and have to wait for another exit point.

I want to transition into stock trading (I know there's a bunch who would like to bust my chops for that:). Another alternative would be to take the gains and 1031 them into more property in a more advantageous market. 

As of now my PITI is ~$1,000/mo. and I can rent each unit for $650/mo. Alternatively (and what i'm currently trying) is to rent the units furnished for $850/mo. to internationals and out of state students (which are drawn to Bethel School of Supernatural Ministry) for 9mo. leases and then listing the units on AirBnB.com for the summer months...?

So i'm weighing out collecting a potential $150k in gains and either begin stock trading (under an experience coach of course), or moving my investing out of state, or possibly holding onto these longer in hopes of further appreciation and having the ability to continue renting to ministry students/families.