I had to go to Texas to get a deal and the base scab that I wanted. I get the need for the screw but I love that ford offers the raptor in scab form. Just my wife and I.
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If you are going from a crew cab to a screw, that's one thing. Its another thing to upgrade for upgrade sake. Not much has changed from 17-19.
How much extra when new was the SCREW cab over the SCAB on the 17 you own? Take that number and add the cost of a low mileage two year extended warranty to your truck so it equals a new 19 in coverage. Then subtract this number from a well negotiated out the door trade in on a new 2019. This final number is the depreciation penalty you are paying for not choosing a 17 SCREW with extended warranty to begin with.
Now consider this......I bought a 19 SCREW coming from a 2014 Silverado crew cab. The rear passenger area is enormous by comparison, like having a small apartment back there. Since total rear space is probably close between my 14 Silverado Crew and a 17 SCAB, I have wondered if I could have gotten by with a SCAB for less money and benefited from the shorter wheelbase break over angle and shorter turning radius. Don't under estimate how much bigger a SCREW might drive and park compared to your SCAB. Also can you organize your existing space better for more room? Take out a seat section you don't need etc.
You mentioned some interest in waiting for the next generation Raptor. If you are likely to buy one you will suffer the steepest part of the depreciation curve twice when you trade up. Once on the 17 and again on the 19.
My suggestion is to buy a 100k miles 4 year extended warranty if repair worries are an issue and hold on to your 17 until the new gen is out. The small performance differences in the 17 vs the 19 aren't worth $18-20k in my opinion. Save it for a Gen 3 Raptor.....
FYI, I received a $5700 discount on my 19 Raptor. Plus a what I believe to be a very fair trade in on my Silverado.
Is there a reason you aren't looking for a used SCREW? If your priority is moving from SCAB to SCREW and aren't really into that new car feel or the differences between 17 and 19, why not wait for the right deal to come along? I get that the market isn't as active in your area, but if you're looking for lowest cost deal, and can be patient, that would be the way to go.
"Nobody" wants a Supercab truck. Yeah, a few of course- but I'm guessing 99% of guys walking onto their lot are not looking for a Supercab. I'll sell it privately first to that unicorn buyer, then go looking for your 2019.