Russell I certainly have entertained that possibility. 2 reasons I am planning to sell now are as follows.......
1. My wife and I are not really willing to "regress" to the point of having tenants live with/next door to us. If it were 10 years ago it would be a totally different story. This is a great strategy but we just don't think we are willing to make that sacrifice.
2. I don't like to bring this "noise" up but I don't have a lot of faith in the market right now. In my area the market is as strong as I have ever seen. I think that a 10K hit in Long term gains tax is worth it to ensure I move this property at the right time. I do not believe in trying to time markets because I'm not that smart, but I do not want to risk a 10% drop in the market as that will eat much of my profit.
Summary-if we are not going to owner occupy the first property there is no tax advantage to waiting. More importantly my whole long term plan rests on this sale, I just want it done!