Expose the USB drive attached to the Pi as a network share via Samba
Map the drive on your Windows PC and point media monkey at it. 
Should all work but the issue is backup. 
A NAS makes the backup task easy as you’d just connect a USB drive and
click a few boxes to schedule a backup.
PiCorePlayer is great but not designed to do be a NAS and while you can
handcode some backup scripts you said no Linux skills. 
Get a decent NAS



VB2.4[/B] STORAGE *QNAP TS419P (NFS)
[B]Living Room* - Joggler & SB3 -> Onkyo TS606 -> Celestion F20s
*Office* - Pi3+Sreen -> Sony TAFE320 -> Celestion F10s / Pi2+DAC & SB3
-> Onkyo CRN755 -> Wharfedale Modus Cubes
*Dining Room* -> SB Boom 
*Kitchen* -> UE Radio (upgraded to SB Radio)
*Bedroom (Bedside)* - Pi2+DAC ->ToppingTP21 ->AKG Headphones
*Bedroom (TV)* - SB Touch ->Sherwood AVR ->Mordaunt Short M10s
Everything controlled by iPeng
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