I've done it 3 times so far...I love Row Venice. I've done the smaller canal tour twice and the cicchetti tour once. I have no desire to row in the Grand Canal with all the motor traffic. The regular tours were more fun for rowing, but pulling the boat in for snacks was great fun too. It was hilarious to see our guide balance a tray full of wine and of cicchetti and hop into the boat with it - I was not ready to manage that successfully!
As far as whether to go together or in separate boats, it can be quite tiring to learn how to balance, keep the oar in the open oarlock, pull it in when passing boats or going under bridges...we were happy to trade off regularly. Everyone got multiple turns to row and to sit and take pictures. But if you're really keen, two in a boat will give you more time to practice what you're taught. I've done it with the five-person boat and with only two of us.
The last time, my friend and I had an apartment in Cannaregio with a large door/window onto one of the canals that Row Venice used regularly. So we got to watch many other people have the same fun we had! I love that nearly all the guides are women. RowVenice is a non-profit designed to financially support competitive female rowers, who don't get the same training and coaching opportunities and whose prize money is a fraction of what the men are paid in the same races.
(Note, I have rowed for over 20 years - the seated and row backwards kind of rowing - so it was especially fun to stand up and row forward and be completely confused about oar handling and port/starboard. Everything was the opposite of my experience so my brain worked as hard as my body!)
Heck, why not take both tours? Do the small canal tour in separate boats and then go out together for the social/snack time. It never got old for me.