I agree with everything you have said. The one caveat is If we extend Stanley it will most likely not start until next season.
True, but that's typically not really relevant.
If you extend him this year, whatever bonus payout he gets is going to kick in immediately, so you'll start prorating that immediately. You don't have to alter his salary at all, but if he has any sort of signing bonus or roster bonus, that will have an impact on current year.
So in Stanley's case, its in their best interest to start it now. He's going to sign for probably at least $18M a year, and his cap hit for 2020 under the option is only $12.8M. It would be highly disappointing to sign him to an extension this year and have his cap hit stay the same or go down. That would be a bad mistake in terms of cap management.
If it were me, I'd be offering like a 4 year, $75M extension, that would keep him here for the next five years. I'd keep his $12.8M salary as is, and I'd give him something like a $20-25M signing bonus. You'd then pickup $4-5M of that this year, pushing his cap hit up to around $17M.
That way you've got a much flatter structure over the length of the deal, making it easier to dump him later if he doesn't perform, and you're only losing like $4-5M in cap space this year that isn't already accounted for.
The overall question I have for this offseason is how much urgency the Ravens are feeling to extend these guys. Stanley is the obvious one, but theoretically, he can be under team control for at least two more years, via the 5th year option in 2020 and a franchise tag in 2021. I'm obviously not a fan of using the tag, but the reality is that in 2021 the OL tag would probably be the neighborhood of $17M. That would be at or below the market value for Stanley currently, who's clearly a top 5 or better LT in the league at this point. So if you're the Ravens, you frankly may not have that much urgency in getting an extension this year, because you can control him for at least two more years.
Same thing with Marlon... under team control for dirt cheap in 2020, 5th year option in 2021, franchise tag available in 2022. He'll get market value sooner rather than later, but with 3 years of team control, is there the urgency to get it done?
The only real urgency I would be seeing is to sign these guys before the price goes up. Stanley is likely a $18M a year player now. Two years from now... north of $20M, easily.
My opinion is they'll wait until the 5th year option year to negotiate with both of these guys. That means Stanley this year, Marlon next year.