I cannot speak to your specific routing, but most systems are not able to handle checking bags through the same airport on the same bag tag (whether on one or more tickets). It is also going to be very hard to obtain a definitive answer from DL because the default customer service answer is "yes" as both are DL tickets.

If you live close to FAR, I would head there and ask a check-in agent (during a non-busy period) as you will get the correct answer.

In any event, you should allow plenty of time at YWG because you will not be connecting and the risk of a no show xYWG is 100% on you.