DD 3.5 or DD 5?

Hello everyone, I'm new to Roll20 and will soon start to GM or a group of friends. I personally am a 3.5 player and GM, but Roll20 seems to be more easy to use with DD5. It has more content available with this version, character sheets seems easier to make, a compendium easier to fill, and potentially easier macros as well. I never played a game on Roll20, only watched a few tutos so far and I am at the point where I ask myself if I should start DMing with 3.5, which is a version I know better system-wise or if I should start with DD5 right from the start, maybe having a bit of a rougher start but easier on the long run? Thanks

I would suggest making a test game for both systems so you might see the differences for yourself.  Anytime you move to a new system there is going to be a learning curve.  IMO coming from 3.5, 5e should be no problem and there's definitely WAY more support for 5e on roll20 currently and moving forward.  Most sheet's make it so you really don't even need to write macros anymore.  Button's on the sheet can be called by their button name and/or dragged to the quickbar(renamed/colorized).  Pro users, through API scripts, can generate chat menus for nearly any sheet as well.  Start small and look into these other features/options as the need arises.  Ask questions on the forums.  Lots of helpful people here.  Good luck and good fortunes.

I was an old school 2nd Edition AD&D player when I first came to Roll20. After playing various 3.5e based video games over the years I jumped into that system two footed and ran a game for 4 years... 5e was very much alive and growing in popularity but I was wary. 3.5e will always be my favourite for the sheer amount of splat it has to make anything mechanically possible but I wish I’d done it all in 5e to save the prep time I used on a veritable monster manual of monsters. There is no right answer beyond what you want to do but as a die hard 3.5e’r I can say with confidence that 5e is a great, easy to use/learn and play system that has the popularity to make running or playing super easy :) Follow your heart!

The third alternative is to try out Pathfinder, which is much closer to 3.5E than 5E, and it have more content as well as an official sheet backing it up.