To test the vacuum advance, pull the hose off the carb and suck on it. With the distributor cap off you should see the plate inside turn as you apply vacuum.
As for constant vacuum to the vacuum advance, there are two schools of thought. I don't like to have vacuum at idle and then have it come in as you apply throttle. Others like vacuum all the time.
But on the 300 six with the Carter YF or YFA, there is frequently no port that gives full manifold vacuum, so you have to use the one they supply.
In any event, you shouldn't need vacuum advance to get it started. It sounds like your timing is late. I'd put it at least at 8 BTDC, if not 12.
Gary, AKA "Gary fellow":
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Dad's: '81 F150 Ranger XLT 4x4: Down for restomod: Full-roller "stroked 351M" w/Trick Flow heads & intake, EEC-V SEFI/E4OD/3.50 gears w/Kevlar clutches
Blue: 2015 F150 Platinum 4x4 SuperCrew wearing Blue Jeans & sporting a 3.5L EB & Max Tow
Big Blue: 1985 F250HD 4x4: 460/ZF5/3.55's, D60 w/Ox locker & 10.25 Sterling/Trutrac, Blue Top & Borgeson, & EEC-V MAF/SEFI