but I have a feeling it will be closer to the third or fourth one.
Yeah...
I think even if there was a big sum to be had, I would likely play it wrong and sell too early.
If it is big enough, early is fine. But, if not, it is going to be painful.
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My whole thing is, to eventually move it out and make it life changing money, it has to be enough that paying the 30% tax on it isn't a big deal. Like losing 300K because you made a million isn't too bad, but losing 30K because you made 100K ends up not being that life changing. At least where I live. Sure it would still pay quite a few bills, but it isn't "life changing".