It is highly recommended to never fall more than three months behind in your bookkeeping.
Case In Point:
The recent COVID-19 outbreak has slowed down the economy and thus has caused a lot of small businesses to file claims for Disaster Relief and Paycheck Protection coverage.
However, like any other request for business financial assistance, the business owner must first present facts about the health of their historical business finances; data typically obtained from financial reports and previously filed tax documents.
If the business owner is behind in their bookkeeping and perhaps tax reporting, they may not have the data at their current disposal to help assist them with these claims. Thus the business owner may be left scrambling to collect the data and begin the long process of correctly booking all of this in a very short period of time. If this happens, then your claim will only get delayed and possibly behind many others who have already filed for similar claims.
So, overall, unless your business has very minimal financial activity to record, I normally recommend to stay on top of your books at least on a monthly basis as you never know when you will need your data.