If you are going to get one...get it now.
The cheapest it will be is in the first year/12K miles. There is a price bump at 12K miles and another at 24K miles if you wait to purchase.
The NEW vehicle ESP (Mopar MaxCare extended
warranty service plan) is retro-active to the day the truck was first purchased from the dealership (in-service date) and overlaps your basic warranty.
The USED vehicle ESP (still Mopar MaxCare) starts the day you purchase the policy.
That seems like it would make sense to wait to purchase since you have 3 years overlapping...but it isn't. You can run the quotes but if you wait until 3 years and 1 day you will pay more for the 4 year used plan than you will for the 7 year new plan.
I read you are looking at Zeigler so it is a factory Mopar MaxCare plan. That is the only one you should consider IMO.
First day rental coverage is a relative term. That's the first day they approve the repair (not when you drop it off unless you want to sit in the waiting room until they give you the thumbs up). I learned that the hard way and dropped my truck off for work with no ride home thinking I was going to get a car to drive. You can rent a car but the day you drop it off is out of your wallet if you don't wait for their blessing. $40 is not a huge deal but if you rent a car and don't wait around but if they don't look at the truck for a week before approving the work then the rental fees are going to start racking up. You only get a maximum of $175 to rent a car for (up to) 5 days and any taxi usage. You can't rent someone's Yugo for 2 weeks and you can't rent a Land Rover for 5 days and expect Mopar to pick up the tab. After taxes and fees $175 doesn't get you very far unless you are scooting around in a Chevy Spark.
True that it is cheaper now. Even without the price bumps prices increase over time regardless. There is also usually a price bump during the summer. If prices spike wait a couple of months and the price will settle down back closer to before the spike.
Wheels/tires and paint are separate policies that you can buy. Most wear items expire after the first year/12K miles so you need a separate policy if you are looking for any coverage that isn't your insurance company or your wallet.
If you sell the truck you get a pro-rated refund. That is based on calendar and not on payout. I had a 7 year MaxCare ESP for my truck and sold it one month shy of 4 years. The work I had done more than payed for the ESP but I was refunded the remaining 3 years I did not use (minus the cancellation fee).
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Also of note is if your truck gets totaled and there is a lienholder then the policy defaults to the lienholder and you are not eligible for any refund.
When I cancelled mine I called Zeigler who I got the ESP through vice going to a local dealership. Process was easy and I had a check in less than a week.