Inspect and clean up connectors to solenoids then swap the fwd and rev connectors and see where that gets you (the wrong direction at best). Might help you isolate the problem point.
Double braid might not be the best bet for this application. Three or eight strand would be preferable. If you intend to use the db it will need to fit through the chain link. If it will fit just use a standard eye splice, but it may hang on the gypsy.
I've got 9 years on Lakes Michigan and Huron with a 410DA powered by CAT 3126TA's (385hp). Trying to sell to move to a trawler but I'm sure going to miss the ride, economy and reliability this boat has provided for long distance family cruising where time has been a factor. And very easy...
Keep an eye on the dates of the 2017 GLCC Rendezvous as space might be tight in Sturgeon Bay during that time. Not many places to overnight on the hook in the SB. Plenty of weeds this year. Suggest you pass into Green Bay and find your way north (17 mi) to Egg Harbor. It is an interesting...
Monitor the fluid level, but if level holds and no shaft rotation in neutral I wouldn't be too concerned. Might learn something from the analysis that helps you understand the cause of the fluid loss. Hope you'll post any findings.