With smaller motorsport AGM batteries, 5 years is a good time to swap it out. If well maintained they could last longer, no doubt, but it's never fun to be stranded somewhere when a preemptive replacement could have taken care of it.
I've bump started the VN once. Took about 5 tries. The most important thing was to basically slam down onto the seat when letting off the clutch to give the most traction on the rear, otherwise she just locks up.
1986 Kawasaki Vulcan 750
NGK Iridium Plugs #7803/DPR7EIX-9
Duralast Gold ETX15 AGM Battery
Coastered & Shaved
Metzeler ME880 [110/90-19, 170/80-15]
Balance Dampers Replaced
Rebuilt Forks w/ Progressive Springs
VN750.com Grill Cover
Emgo 23-92411 Handlebars
MOSFET FH012AA R/R
1990 Kawasaki Vulcan 750
1998 Honda VFR800 FI
2014 Honda VFR800F
1989 Pontiac Firebird Formula 350