Hi,
I am currently using a community version and am planning on upgrading the site to the fuller version later once the site gets going and it's making money.
Question: Should i even bother doing this? Or should I just upgrade from now and save future hassles.
If not, or if so, please explain so I get a better understanding.
I think that’s a question only you can answer. 
What do you need the site to do? Does the Pro version have features you really need?
I would think it easier to upgrade the site now whilst your starting out compared to doing it later with a really busy site that might lead to some downtime.