Other than the audio problem and some rule mishaps (you corrected your self later on) it was quite entertaining.
Sure, there wasn't opportunity for huge RP moments, but what you got from dice rolls was quite funny. (Guybrush getting 2 hit KO'ed by a goblin ).
Hm, I guess it pays to have in mind that you can split your movement between your attacks and actions (like fighter's extra attacks, or two weapon fighting). So you don't have to unload everything against one target. Oh and that creatures also provide cover, friend or foe, they give half-cover.
Regarding the system. Overall I like the streamlined parts. That everything keys off proficiency bonus and your ability modifier. Only adding some extra stuff in certain circumstances. Or how the different pluses and minuses are replaced with all encompassing advantage/disadvantage. This is even when factoring "resistance". As you don't have to keep track of actual numbers (like resist 10 radiant, 5 fire, etc). Now it's only "if creature resist something, they take half-damage of that". Sure, you can't have situations where you ignore small amounts of damage and mitigate larger ones. But overall it sure does keep down the bookkeeping, so I think the trade off is worth it.
If people want even more streamlined system, I would recommend Dungeon World. I have been playing and enjoying it past few months with my group. It is quite different system than you average simulation RPG (like D&D).
Oh, regarding roll20. I would suggest making macros for the most common actions you would be doing. Like initiative, attacks and damage. There are some nifty things you can do.