Okay, so to get the calculator “accurate,” uncheck the zero drive-off box, and add everything that is rolled in - doc fees, etc. (acq will be included when you don’t check that box) - and put the first month’s payment in the down payment box. It might then say you owe $25 in taxes or something at signing, so ignore that.
I prefer to do leases with no more than $1,000 DAS, but when you roll more things in and you’re doing MSDs, the MSD amount becomes higher.
Here’s a way to think about things. If you don’t do MSDs, and you roll in all your costs, say you do a pull-ahead with 6 months left on your lease. You are not paying 1/6 of the cost of whatever is rolled in, and you come out ahead anyway.
Case-in-point: I just pulled ahead 4 payments on my 2017 S60. I had rolled in NY tax, which was about $35/mo. I saved $140 of the tax due, more than 10% of what I rolled in.
I did buy the wheel and tire package separately on my car (at cost, though) because the roads in NY and NJ are getting worse and worse, I hit a massive pothole last year, and the garage at work did a number on my old wheels (luckily not charged, was worried). With the 19" wheels I’d be insane to not do it. Rolling it in would have raised my payment by $22/month, and then if I pulled ahead, I would be saving a chunk of that, let’s say $90 if I go 4 months early again. I just didn’t want to increase my payment any more, and I paid with a credit card where I got 3% back, so I got the equivalent of $44 cash back anyway. If I transfer to JetBlue, I know that the 4,300 points translates to a free flight ($65 flight is 3,800), so it was a no-brainer to not roll that in. (If you’re doing the math, yes that’s about $1,400 charged - my DAS for the car was $675, plus the cost of the wheel and tire package, plus tax.)
Sorry for the long explanation, but I feel examples are helpful.