So long story short, a friend owed me for a favor and since I did not have bitcoin before he asked If I would take it in BTC. I didn't mind since I can cash out whenever.
My question is.. what do you think? Its a decent chunk of money for me to just hope something keeps rising, do you think I should "let it ride" or cash out and just be happy with ~$500?
The decision depends on you. If you really need money for various needs then you should immediately sell the bitcoin you receive it but if you do not need money in the near future then I advise to trade or you can hold it as an investment and expect bitcoin prices to rise. However, if I become in your current position then I will sell half of the bitcoin received and the other half will be made as an investment.