After finding out my competitors pricing was 300% higher up front, should I increase the cost so I don't seem "cheap" even though our monthly saas costs will make up for it?
What you should do is price vs. your perceived comps.
Are you “better” than this competitor? If so, charge more.
Are you “more enterprise”? If so, charge more, at least, for larger customers.
Are you “more secure”? Etc. etc.
If you aren’t better, more enterprise, etc. Just different.
Then just stick to what’s working.