depends on how long you wanna hold your caoins and how fast you need to react to price speculation...the last altseason it was clever to have multiple sell orders in the market, especially in the bull run November/December2017. But that means you have to hold your coins on the exchange itsself....also some smaller coins in my wallets are making forks and upgrading their chain so if you are not "up to date" with each project you may get in trouble.
Yes, depends on what the token you bought and what are your expectations into it. That is why many of the long term investors ended up losing their money because they are not researching well on what they are wanted to buy or what they are buying. There are some factors into it right.
If you ever hold coins make sure it is multiple I suggest and not just one because when the market goes up for sure all of the tokens or coins you have would follow the trend.