It will be quite similar, and depends on the market, assuming you aren't selling, because the appraiser is essentially the one who holds your returns in their hands.

In 5-8 years I’d love to be living there again with a handful of rentals under my belt.

Also, she thinks taking $10K cash on the weekend means she will check if the cash is real on Monday after handing over the keys.

They were both very certain of this.My accountant on the other hand says that I can and it just has to go into any IRA.Do you guys know whether or not this is correct?

Does anyone have a first hand seller financing story they could share?

Some people are more risk averse than others so as you thought my answer is it depends. the seller is firm on his price have you asked if he would be willing to try and hand over the property vacant?

I was rather young for the 2008 crash so I don’t have the hands on experience in a down market.

Plus I can bring the city down on them when they get out of hand.

If you’re planning on moving at that time, I highly suggest to start looking around 1-2 months before hand and give  your landlord written notice that you are not going to renew the lease.   

On the other hand, if they are only 15 years old you may spread that cost over the next 5 years.Turnover costs really depend on the tenant quality and the length of time they stay.