Eligibility for stock rights offering
Yes, there is a delay between when you buy a stock and when you actually take ownership of it.  This is called the settlement period. The settlement period for US equities is T+2 (other markets have different settlement periods), meaning you don't actually become a shareholder of record until 2 business days after you buy.  Conversely, you don't stop being a shareholder of record until 2 business days after you sell. Presumably at some point in the (far) future all public markets will move to same-day changes of ownership, at which point companies will stop making announcements of the form all shareholders of record as of September 22nd and will switch to announcements of the form all shareholders of record as of September 22nd at 13:00 UTC
Unfortunately you can't use your HSA to pay for expenses in year A. Qualified medical expenses for an HSA must occur after the date the HSA account was established. (Established typically means the date the account was opened in your name.) The other answers already mostly answered your other questions, but I want to really hit home some particular points that many people may not realize: The most important thing to do when you are eligible to have an HSA account, is to open an HSA account ASAP. This is true even if you don't put any money in it and you leave it empty for years. The reason is that once the account is established, all qualified medical expenses that occur after that date are eligible for distributions, even if you wait years before you fund your HSA account. The second most important thing to do is to keep track of all out of pocket medical expenses you incur after you open the HSA account. All you need is a simple spreadsheet and a place to store your receipts. Once you have the account and are tracking expenses, now you can put money into your HSA and take it out whenever you'd like. (With limits- you can't put in more than the contribution limit for a single tax year, and you can't take out more than your eligible expenses to date.) Helpful Tip: Many people don't fund their HSA because they can't afford to set aside extra money to do so. Fortunately, you don't have to. For example, suppose you have some dental work and it costs you $500. Once you get the bill, before you pay it, put the $500 into your HSA account. The next day, take the $500 back out and pay your dental bill with it. Most HSA accounts will give you a debit card to make this even easier to pay the bill. By putting the money into your HSA for 1 day you just received a $500 tax deduction. Alternatively you can always pay out of pocket like you normally would, track your receipts, and wait until the end of the year (or up until April 15 of the next year). I like this option because I can pay all of my medical bills with a credit card and get cash back. Then at the end of the year, I add up the expenses, deposit that much into my HSA, and if I'd rather put that money somewhere else I just pull it out the next day. If you decide you don't need the money right away that's even better since you can leave it in the HSA account and invest it. Like a Roth account, you don't pay tax on the growth you achieve inside of an HSA. Another Tip: if your employer offers the service of automatically making deposits into your HSA by reducing your paycheck, you should definitely try to do that if you can afford it, rather than manually making contributions as I described in the previous tip. When your employer makes the contributions for you, your wages are reduced by that amount on your W2, so you end up saving an additional 7% in FICA taxes. Unless you own a business and the car is used in that business you can't write off your auto repairs. If you start a sole-proprietorship in your own name there are all sorts of things you can write off as long as there is a reasonable expectation of profit. This includes a portion of your car repairs, a portion of your home expenses (assuming it's a home-based business), any tools used in the business, all kinds of stuff. The portion of your auto is based on total miles driven in the year vs. total miles driven for business purposes. Eligible auto expenses include repairs, gas/oil, insurance, parking, and interest on the auto loan. There are some things to remember: I'm no expert on California business law. Talk to a lawyer and an accountant if you wish to go this way. Many offer a half-hour free session for new clients. Summarized article: The NASDAQ announced it will offer $40 million to compensate clients who were disadvantaged by technical problems during Facebook's IPO on May 18.   NASDAQ's technical glitch caused a delay in the opening of first day trading of Facebook shares and traders experienced slow order confirmations.   NASDAQ said $13.7 million will be paid to its affected investment firms and the balance will be given to the firms as credit to reduce trading fees. The benefits would last as long as 6 months.   Investors who are eligible for compensation are those who placed orders to buy Facebook shares at $42 or less but were executed at an inferior price or those whose orders went through but were not immediately confirmed.  The New York Stock Exchange (NYSE) opposed the compensation offer saying the move would allow NASDAQ to undercut them on prices and would take market share from competing exchanges.   NASDAQ's compensation plan is subject to regulator approval.    Facebook shares are currently down 30% from the IPO price of $38.  *For more summarized news, subscribe to the [/r/SkimThat](http://www.reddit.com/r/SkimThat) subreddit* "The stock market is not a zero-sum game.  Some parts are (forex, some option trading), but plain old stock trading is not zero sum. That is to say, if you were to invest ""at random"", you would on average make money.  That's because the market as a whole makes money - it goes up over time (6-10% annually, averaged over time).  That's because you're not just gambling when you buy a stock; you're actually contributing money to a company (directly or indirectly), which it uses to fund activities that (on average) make money.  When you buy Caterpillar stock, you're indirectly funding Caterpillar building tractors, which they then sell for a profit, and thus your stock appreciates in value.  While not every company makes a profit, and thus not every stock appreciates in true value, the average one does. To some extent, buying index funds is pretty close to ""investing at random"".  It has a far lower risk quotient, of course, since you're not buying a few stocks at random but instead are buying all stocks in an index; but buying stocks from the S&P 500 at random would on average give the same return as VOO (with way more volatility). So for one, you definitely could do worse than 50/50; if you simply sold the market short (sold random stocks short), you would lose money over time on average, above and beyond the transaction cost, since the market will go up over time on average. Secondly, there is the consideration of limited and unlimited gains or losses. Some trades, specifically some option trades, have limited potential gains, and unlimited potential losses. Take for example, a simple call option.  If you sell a naked call option - meaning you sell a call option but don't own the stock - for $100, at a strike price of $20, for 100 shares, you make money as long as the price of that stock is under $21.  You have a potential to make $100, because that's what you sold it for; if the price is under $20, it's not exercised, and you just get that $100, free.   But, on the other hand, if the stock goes up, you could potentially be out any amount of money.  If the stock trades at $24, you're out $400-100 = $300, right?  (Plus transaction costs.)   But what if it trades at $60?  Or $100?  Or $10000?  You're still out 100 * that amount, so in the latter case, $1 million.  It's not likely to trade at that point, but it could. If you were to trade ""at random"", you'd probably run into one of those types of situations.  That's because there are lots of potential trades out there that nobody expects anyone to take - but that doesn't mean that people wouldn't be happy to take your money if you offered it to them.   That's the reason your 16.66 vs 83.33 argument is faulty:  you're absolutely right that if there were a consistently losing line, that the consistently winning line would exist, but that requires someone that is willing to take the losing line.  Trades require two actors, one on each side; if you're willing to be the patsy, there's always someone happy to take advantage of you, but you might not get a patsy." Note that your link shows the shares as of March 31, 2016 while http://uniselect.com/content/files/Press-release/Press-Release-Q1-2016-Final.pdf notes a 2-for-1 stock split so thus you have to double the shares to get the proper number is what you are missing. The stock split occurred in May and thus is after the deadline that you quoted. It might, but it also might not. The Board of Directors gets to decide whether and how much dividends are paid to stockholders. So this will vary from company to company and may change over time. I suggest you ask the person making the offer. That said: It looks like they offered you OPTIONS, not Shares. An option is just the right to buy stock at a given price in the future. It is extremely unlikely that you would be entitled to any dividends since you don't have an ownership stake, just a potential to be a shareholder. After a company goes public, if it wants to raise more money, then it does this by secondary public offering or rights issue. In subscription rights issue gives the right to existing share holders to buy new shares at equal proportion. So if every one buys, they maintain the same percentage of ownership. Generally the pricing is at discount to current market price. Not sure why the price is high, unless the price for this stock fell sharply recently. ASSUMING THIS IS A QUESTION OF U.S. SECURITIES LAWS You didn't explain whether you're related to the mother and son, but I'll assume you are.  If that's the case, this really wouldn't qualify as a solicited sale.  It wasn't advertised publicly for sale, and there is already (I assume) a long-standing relationship between the parties.  In such a case, this would be a perfectly legal and normal type of transaction, so I can't see any reason for concern.   That being said, you would be wise to contact the state securities regulation agency where you live to ensure you're on firm ground. The law pertaining to the solicited sale of securities normally targets instances where people are trying to do private stock offerings and are seeking investors, in which case there are a number of different state and federal agencies and regulations that come into play.  The situation you've described does not fall under these types of scenarios. Good luck!