There should be a company policy on tips, rather if the tips belong to the restaurant (over the counter), the waiter/ waitress (which could then be payroll), or whatever the arrangement is. If it does belong to payroll, your company should then recognize it as income but then journal entry to pass onto the employee. There should be some sort of tracking report and be issued and sign off periodically (and for tax purposes).
Cash over /short should be minimum, assuming they count the cash before and after everyday. Obviously things and accident happens, like miscounted or wrong change. In this case check the restaurant policy, sometimes they just write it off as a loss, sometimes the policy was whoever was on duty that period need to make up that sum (if over certain amount).
There's nothing wrong with doing it monthly, depending how much sales you have and the amount. In small companies it's not unusually they do everything once a month and just one huge 50 line journal entry. This happens often if they have manual invoice or used a different system. However, you should be aware that X amount of sale tax applied after you exceed certain amount of sales, and other things start to kick in (and different state might have different policies), so you want to make sure you don't missed that deadline.
Financial statements should come automatically, to keep it simple you should have only several big income and expenses account, and then have sub-income and sub-expense account under those, and then maybe divided them by location or use the “name” function to sort. If you file everything correctly the statement will print out correctly without a pain.
New York - NYC
Passed CPA Exam (11/2014)
In search for a position in NYC that will fulfills the license requirement.