Likelihood of waitlist coming through

I'm hoping someone can give some advice about waitlisting. In 22 years of using DVC, we've never done it before.

We need (2) 2 bedrooms at BLT. I booked one standard view no problem. I went to book the other and I could book all but our arrival night (Friday) in a standard view. Which makes me think that I got the last standard view for that night, so we'd be #1 in line if someone else cancelled right?
Should I book the remaining days and wait list our arrival night? What are the chances that it'll come through you think? Or should I just book the lake view for the entire stay to be safe?
With our group, we want to be in the same resort, and this group will not want to move rooms.

BTW - our 7 month window just opened up on Monday, and these points are one borrow points so there's not turning back once I book a lake view.

Thanks for any help you can offer!

I think chances are good that the waitlist will come through. I would book the first night lake view and the rest standard view. Then, I would waitlist the first night in standard view and have it replace your lake view night. I think your waitlist will come through, but it would give you something for that first night, just in case.

I've had success with single night waitlists, especially around the 7 month mark.

I would book the remaining nights as standard view and book the first night at another resort.
Waitlist the first night.
If it doesn't come through then get a dining plan for the first night and splurge on good food!