Yaz, I don't pretend to be an "expert" but I do know my way around investing - Interested in getting your point of view.
This scenario is under the, what i believe to be unlikely, assumption that we don't see a penny again until next year [we will see it. . just don't know when].
. . My only issue with ILIV is that I'm on a timeline, 12/31 - As I'm playing with all profit money should I hold till 1/1/15 I'm out $8,000 in taxes on this "profit" that is very obviously worth 25% of its actual value - Now I could pay that no problem, but of course if I pay it and than sell ILIV for a loss I end up getting screwed - Or I could sell on 12/31/14, harvest the loss - feasibly break even and run the risk of it jumping crazy amounts before I can rebuy it without tax implications [30 days].
What I was considering doing, but haven't fully fleshed out the idea just yet, as I only brought it up while driving to work. . .
Is using a secondary brokerage to purchase more shares [I have a scottrade account but would probably look for something that doesn't charge a premium for penny stocks]. . .Instead of flipping those shares when it jumps 10-30% on huge swing selling my old shares for a loss slowly. In essence recycling my old shares over time to lower my tax implication but keeping my share count fundamentally the same [1.5million shares].
The only 2 downsides I can see are:
1) Running the risk of it dumping again - Which i'm not too worried about, I'm pretty good at seeing the flip opportunities, I usually just try to go for the big picture.
2) In the end when ILIV does jump to where I would break even more of the money costbasis wise would be profit driven - But I think if I'm doing the math correctly in my head since it was all profit money anyway that would just even out to roughly the same $8-9k.
As someone who clearly knows more than I do about the whole investing world - What are your thoughts?