Some early advice to you indicated the Winn system has proven to be problematic for some folks. It appears the Winn has been involved in your situation as well. It is never advised to "double" the gaskets on a fuel filter to try to stop leaks.
If I were you, I would get a new fuel filter head with screw-on filters to replace the Winn system.
A fuel pressure gauge can be very useful in diagnosing a fuel supply problem. It can indicate clogged fuel filters, a failing fuel pump, or whatever by showing a problem with fuel delivery pressure. But it won't fix your Winn system if it is causing air leaks in your fuel supply.