It is hard to tell based on original post and without seeing the portfolio quality and quantity. A few months is a pretty short timeline. I measure profit by year, and frequently have slow periods of a few months where money going out is more than what came in, but I have never had an entire year where I lost money.
If he is leveraging all the money coming in without setting aside operating capital, he may need to add capital. It goes back to number 4 - he needs to figure out his business model.
When I make sales, my first allocation of money is to renewals. In good times, I like to be 6 months ahead on renewals. Then I spend part on more names and/or pocket some. Being less than 3-4 months out on my renewals is my trigger for dropping/dumping lower quality names, looking at pricing, etc..