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Last Friday I traded some VXX puts after the market close(trades like 15 min from 4-4.15pm). They were out of money by 4.15, so didn't bother to close. Come Monday and my puts were exercised, luckily i had enough to cover. Turns out the settlement value of those options is determined by the...

its called leverage

just because there are no bids doesn't mean there is no liquidity, it just depends on if you are in the money or not, if you are ITM, try placing a limit order, of-course you have to roughly know the option value. Have traded a lot of those positions where there are no bids/no volume or open...

depends on what you trade, if its SPX or some other liquid instrument its not an issue exiting a position

unless you day trading over 2k contracts in an illiquid instrument you should be good

you didn't mention what you want to trade, options or the underlying

tax selling, try doing that on normal expiration day, it moves cents killing both near otm puts and calls

From my experience most of the time SPX is usually flat on Mon/Wed/Friday expiration takes some news/event like tax reform or fed or tax selling etc to move it, usually its struck between strike prices.