Ask him if he is VIP gold or silver?. That gives the ownership a great deal more value if any family member can be added to the deed. Do you have any aunts, uncles, cousins that might be interested in it? He wouldn't be selling it to them just adding family to the deed giving them rights of survivorship.
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I'm guessing that his loan is for the 400,000 Wyndham points. Are the PIC contracts paid for and where are they at? Does $2700 include the maintenance fees on his PIC contracts. They are paid to the individual resorts and wouldn't be included in his Wyndham fees except for the annual fee to keep them in the PIC program. Taking them out of the PIC program might take him out of the VIP program but would reduce his Wyndham maintenance fees. You need to know what the individual maintenance fees are on each of the three because they can get sold or given away separately and need not be tied to the Wyndham deal. If either of the PIC resorts are in RCI it might be worth it for you or your sister to keep the cheapest one. You can get some really cheap nice vacations through RCI.
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Also make sure you find out what options, if any, are open to him through Ovations for the Wyndham deed.
Jan's question about the PICs are important. With the PIC contracts transfer and kept to KEEP GOLD VIP ... you would have a great level for family vacations. What their MFs for those 2 timeshares, would increase the YEARLY MFs costs in addition to the Wyndham ownership.
Also ... find the DATE of those PIC contracts conversions ... the PIC program CHANGED a few years ago .. to be only for a LIMITED time option. Another "taste" or "hook" to a higher level setting up the owner to BUY more direct Wyndham points.
If your family is limited on paying for MFs ... now is the time to DUMP (refuse inheriting those 2 PIC weeks ownership).
400K in Wyndham points is still SILVER VIP ... 25% discount of reservations BOOKED inside of 60 days with free unit upgrade at 30 days out from checkin if available.. if YOU via the online system 'upgrade button. GOLD offers 35% discount and at 45 days out from checkin, free upgrade if available.
There are other pluses over GOLD verses SILVER.. but the real questions iare, can you pay the 2 weeks which are not included with Wyndham MFs ? AND do you truly NEED 700K of Wyndham points to use each year?
Additionally, you should look at whether you would use the PIC weeks over the Wyndham points ... and decide to walk away from Wyndham ponts but take 1 or both PIC weeks?