This is a bad idea if you NEED to SELL your current vehicle to get it. I say it is better to wait for one in your area to pop up. If you place yourself on the artifical timeline, then you are going to mentally force yourself to be ok with it.
Then, in 2 months, when the shine has worn off and you notice all the things that are not OK with it and you start *****ing on here, you will get a lot of people commenting on how you should have waited.
Also. If this is to be your daily driver and you really need to rely on it, why would you buy it sight unseen? The problem for you is you need to sell your current truck to afford the new one, that means you will be in a bind if this goes south.
So. MY personal opinion? There will be one, closer, and better at some point. Don't rush.
That said. You have missed all the important stuff, so gonna assume you are young and new to this.
You said NOTHING about a 3rd party inspection. I mean a serious, YOU PAY FOR IT, inspection to find any and ALL issues. You can pay the nearest Toyota dealership about 150 bucks to give it as complete an inspection as possible. Make sure they have a body shop and throw it up on the rack to look for body damage.
Second. Have you PULLED all the records you can for it? From Toyota and from Carfax? If you haven't, then how can you EVEN be thinking this is a good idea. Someone on here just discovered from the Toyota site that a truck they recently bought doesn't even have the original transmission.
Do you DUE DILIGENCE and slow down.
As for what you ask him, you ask him everything. It is against the law for him to LIE to promote a sell, that is called Fraud. So, you type of a sheet with a bunch of questions.
1. Ever been in an accident?
2. Any large issues ever popped up?
3. Have you ever neglected maintenance (a.k.a gone over the Oil interval)
4. etc,etc.etc.
Then you have him SIGN and DATE it at his nearest notary...
Also. You never EVER negotiate price before you see it.. that's just dumb. If you don't care, then sure...
But.. again. I think these long distance, sell your own first, desperate plans are a BAD IDEA.