Re: 2 batteries?
depends on what you are using and how.
Any motor under 25 can be pull started and doesn't need a battery, so there's little risk from running the battery down.
How far down the battery will drain while trolling depends on a dozen factors, none of which are revealed in your question, so to answer yours, you get the best answer to every boating question: it depends!
Starters require a certain threshold of voltage to work, so sometimes a weak battery will work other things but not the starter. Also a motor that has been run starts easier than a cold one and thus requires less of the starter.
Experiment but have back-up while you do.