What Problem, if fixed, would make you sleep better at night?

I'm new to the community my husband is a retired military looking at starting his own business in the construction industry (roofing being the main focus).  I would like to get some insights from this forum and get ahead of some of the issues and problems we might face going forward.  I appreciate any feedback as to what problems you have right now that keeps you up at night about the roofing business.