My comments will align with some of the comments above, and this is an issue I've seen a number of times consulting for small start-up projects.
I like to break this into a series of questions you can ask yourself:
1. Is there any way that V2 can be successful if V1 fails to get traction? If V1's success is the only path to V2, then priorities are easy: V1 has to get what it needs because if it fails nothing else matters.
2. How much user feedback do you have on V1's making users happy? Before we even get to monetization we have to make users want to come back the next day to use the service again, and we have to make them want to tell their friends how great V1 is. Without this kind of response monetization is a moot point. If you haven't gone through the cycle of tuning in V1 so that it thrills your initial users I think you MUST have a plan that gives you both access and time to do so. Otherwise you're basing everything on an untested plan, and in 25+ years of building online apps I've rarely seen an original vision that did not change a lot once we got real user feedback.
3. Now we get to monetization. Have you had the chance to run tests on monetization of features and/or services from V1? If not, that's another area where you want to have had the chance to tune things with real customers before doubling down on your bets.
4. Do you have time/resources to do a narrow territory rollout of V1? For example, if you have the resources to do so you could do a rollout in Australia and New Zealand and perfect things there, while (to Kristann's point re messaging) preserving your options on market positioning in larger markets like North America. You can also go live in Canada before doing the US for the same purpose.
Hope this helps!