Ok so I have made +30% on a stock and would like to start selling covered calls because it's at its 52 week high but I don't want to just sell it. I plan on holding 5-10+ years and adding throughout time. Would it be a good idea to sell these covered calls OTM? Also if those covered calls become ITM what happens to my shares? Then what would happen if they become OTM again (I.e 5 day before expectoration, strike = 10, stock hits 11 then next day goes to 9) ? I guess I'm confused with the ownership during price action and if person exercises shares vs just trading/selling away the contract.
I wouldn't sell Covered Calls on a stock you plan on holding for 10 years. As for the rest of your question it's just a matter of accepting the outcome of the trade. It should make no difference to you if the stock gets called away or it doesn't - otherwise don't sell Covered Calls, or buy-to-close the options if they hit ATM.
It is unlikely that you'd get called before expiration on your calls. Go reasonably OTM but realize that there is not going to be a lot of upside premium to be had. It would help if we knew the share ticker and vol-line. You will lose your shares at the strike price of the call you're short if the call is ITM on the close of the last trading day. You may lose them earlier, depending on real and synthetic rates (dividend stuff). Anyway, that's not much of a concern as you can simply buy the shares or sell a put (same concept, fungible). You can also sell two OTM calls to convert the long shares into a short straddle. Further, you can buy a deeper call and a deep OTM put to convert the straddle to a fly. Lots of possibilities. I would recommend going as far out on duration as you're comfortable, especially if the shares are volatile. You will have a mark to mkt PNL, but you cannot be forced to cover the short call. It will always reduce the haircut on the shares.
I would consider taking the 30% profit, especially if it's at a 52 wk high. Won't stay up forever. Watch the volume for a possible easing off the high. Check out some TA, like 200 sma's, candlesticks and microscope the fundamentals (especially cash flow statement) etc. Money can be reinvested for faster compound. If your adamant on writing calls, if bullish just OTM, bearish, just ITM (front month) Cheers