I will try and take a stab at these:
1. How long does an average re-sale purchase take?
Roughly 2 months from start to finish. ROFR can be quick, but may take 30 days. Once that clears, you have to go through closing (about 2 weeks) and then maybe another week to get your member number (this is all variable though).
2. What are average closing costs? Is it possible to negotiate that the seller pay these?
It depends on the number of points you buy. I would say between $375 and $550. Everything is negotiable, but the ROFR is looking at EVERYTHING when they look at your deal.
3. Assuming we have a resale contract with current year points, how quickly can we access those points?
Again, once you get that member number, then you can make a reservation.
4. Regarding use year and cancelled trips, if we cancel a trip and are not able to use them before our year ends can't we just bank them for next year? If not, could we rent them?
There are banking windows which are as follows: within the first 6 months following your use year, you can bank 100% of that years points. Within 6 to 9 months of your use year, you can bank up to 50% of that years points. In the 10th month of your use year, you can bank 25% of that years points. In the last 2 months, you can not bank any points from that year. Finally, yes you can rent them out, but I believe this is really difficult if you cancel in the last 2 months.
5. What are everyone's thoughts about re-sale vs. SS with the extended expiration date?
IMHO, it really matters where you want to stay!! If you want SSR then I would go with it. If you want somewhere else, then go with that. I would figure out your age in those last few years and see if you think it will really make a big difference to you when you are 60, 70 or 80 years old(or older/younger, not sure what age you are now).
