Advice Wanted - Hold, Sell Now, or Sell Later

[John Thomas]

What Would You Do?

I have a rental that breaks even monthly, but the loan is adjusting in 6 months which will make me go negative by $300 to $400.  I bought it as a primary residence years ago and transitioned it into a rental 18 months ago when I bought a new primary.  I paid way too much for it (in 2005) so I have come to grips with the fact that it will not appreciate back to that point.  There is still some equity though.

I never intended it to be a rental and want to sell it and use the funds to start flipping.  HERE IS THE PROBLEM - the lease just expired and the tenants want another year term.  If I'm selling it soon, I can't lock in to a year but it would be nice to ensure the place is rented while on the market so the mortgage is covered.  

It seems counter-intuitive to hold it knowing the loan is adjusting upwards and 2005 values are long gone.

Should I go month to month or year term and place it on the market now or later?  

All advice is welcomed!