In the event of a temporary short squeeze, what are your thoughts on selling some of your position during the peak? Will a re-buy in at (420?) be possible? Is it worth the gamble? Perhaps we will be able to reinvest at the 6-month liquidation events once private?
Trying my best here to strategize, I am not real liquid right now and can't add much to my meager position but if the opportunity arises can I buy additional shares (after or before) Privatization and what might those buy-in limits be?
The only answer you can trust, today, is "nobody knows". There's no actual proposal with details.
That being said, I would lean heavily towards not trying to sell at some peak with an expectation of buying back in, if what you really want is to be part of the private company (this happens to be where I want to end up). If there's a squeeze, that specifically means there aren't shares to be bought, so the people that HAVE to buy are now offering more and more money to find people that will sell. In theory, there might be a sliver of time where all the people that HAVE to buy do so at higher prices, then the price falls back down to $420, AND THEN you can still find new seller that didn't / wouldn't sell at the higher prices that are now willing to sell at $420.
It COULD happen. I'm thinking, very unlikely
A good reason to sell during a squeeze is to raise cash now that you want / need. But if this is a holding where you're thinking 10+ years investment scale, then a spike from 400 to 800 and back down again, is just a speed bump hardly worth slowing down for.
A different but related idea - if your investment horizon is long (many years, decade, +), then in some ways, Tesla is hard as an investment. It's so volatile, it's hard not to get caught up in day and short term trading all that volatility. To be a long term buy and hold for Tesla, you need a clear idea of your long term investment thesis, do your daily monitoring in terms of that long term investment thesis, and realize that whether today's stock price starts with a 2, 3, or 4 - it's all just noise. (At least for my investment thesis, until the 2/3/4 has 3 digits after it, it's still just noise). $50 up today and $50 down tomorrow - more noise.
It can be hard to remain convinced that a 10-20% move in one day is still just noise
(All just my opinion, but I'm long in shares with a 10+ year investment horizon after holding for 5 years so far, and also with OTM '20 calls that likely became worthless with the go-private announcement, but I'm holding them for now because there STILL isn't an actual deal / offer, with actual details, on the table)