The big issue that you may confront is that the IRS could choose to treat one of your long term profitable investments as short term, so you would have taxable income even though you didn't sell the stock. However, as long as you accurately account for long term investments by indicating them as such, this should not be a problem. Re the Sub S corp. and liability protection, if you are the 100% controlling shareholder, and you are involved in a traffic accident from which the other party is seriously injured and obtains a judgment against you for negligence, those shares which are personal property to you would be subject to execution/garnishment to satisfy the judgment. So, the corp entity would not protect your assets. If, your vehicle is owned by your company, then that is still insufficient protection, as the party who sues you would sue you personally AND as the president of the corp, and could thereby reach both you and the corp assets. The only real insurance against liability such as you describe is a liability insurance policy, OR, an offshore comp in a jurisdiction that is extremely hostile to creditor attacks (e.g., Isle of Nevis).
What if it is a nevada C corp....From what I understand your ownership of such a corp would not show up in an asset search. I am thinking of puting realestate in a nevada C corp for asset protection.. Nick