Although I agree with your logic, when you find the used truck that you really want for all of the reasons, waiting can be a solid disappointment. On the other hand, jumping can be very injurious! It's a toss up. I don't know where the OP is located, but here in Florida there are quite a few...
If you live only to wait for the next breakdown, you will never enjoy your ride. Having a garage full of vehicles only means you have a storage lot! Drive, enjoy, and maybe cross your fingers all the while you are building a small contingency fund.
The door keypad is on my list of changes to my Ranger. The IA key would be nice too but I didn't want a Lariat. I do have one of those magnetic keyholders too. Usually one of the earliest additions to a new to me vehicle.
I can think of many negatives, including the one you mentioned, but no real positives. The weather to be a huge bummer. And you are advertising that something of value is attached to your rear bumper! Plus spending that much cash for a FOB, plus programming just to hope it doesn't get stolen...