I have a number of weeks some, enrolled done when the option was initially available in 2010 for the fee at the time, and some not. I have intentions of getting the others (all resale purchases) enrolled partly for current additional options and partly for legacy planning with the adult children (long story, another thread). So last summer we went to a couple of tours when in HI to gather information in addition to what was posted here. At the time the option to enroll for the 5500 points was on the table. Apparently there they did not have the purchase enroll option but I could have gotten it through internet sales or working with Aruba I'm sure but at the time I only wanted information as financially we weren't ready so I didn't put a lot of additional time or work into pursuing further. So in January we were in Aruba and I went over and talked to a sales supervisor (uncompensated, just me) and inquired about the possibilities in the future based on past promotions including doing the 7.5 weeks instead of 7, nothing was going on at that time. I expressed interest in a future option but again, finances were a consideration so 1-2 years would be our timeframe anyway.
So recently I was contacted by Aruba saying the promotion was back on. Apparently there is a minimum dollar amount to do this and enroll much along the lines of the purchase requirements doing so on points. The first offer was two Gold weeks at SC totaling 4625 destination points and a total costs of $49K. I let them know I had no interest in Gold weeks or 2 weeks (and dues on 2 weeks) but I would have interest in Platinum or possibly Platinum Plus. So they contacted me a week or so later saying they now had an OC Platinum week but given the dollars it didn't quite meet the minimum so I'd have to buy 250 trust points also to qualify. I did agree as I was planning to do so even with points at some time in the future when finances were more favorable and comparatively speaking, this was both better and cheaper for me as we go to Aruba every 2-3 years anyway. As we were in the process they came back with a 3 BR Platinum at SC which would be a little cheaper than the OC + points and it would remove the requirement for the trust points (and 2 closings). The 3 BR & SC are both better choices for us and the modestly lower price was also a plus so we made the change. They did have to get approval to do the 7.5 weeks over just the 7 but that went through quickly and would have been foolish on their end not to agree. Incentives varied slightly but in general were an extra set of DC points good for 2 years just above a years worth looking at the week purchase. There was also a finance incentive equaling a years worth of DC points after 18 months which I'm declining. I can look at the 3 offers if anyone wants specifics.
So just looking at the 7.5 weeks I'm converting added to the SC 3 BR and including acquisition costs on all, I'll be under $3.5 pp cost and under 38¢ pp dues (for either platinum choice). But it's still a chunk of change and something I didn't have to do. And one might argue an unreasonable expense since I'm already chairman's club and that would be a fair position and one I've gone back and forth on over the past year or so.
It does bring up an interesting gamble scenario for one who's new or newer to the game and interested in getting into points. One could buy resale weeks that are lower cost, lower comparative dues and higher DC points getting to 7-8 total non qualified weeks (EOY weeks count as 1/2) then potentially do this type of conversion next year or the year after if available, or just buy points. For sake of discussion if one bought 7 Vegas 2BR Platinum and enrolled with a $50K week that brought them in the total acquisition cost would be around $80K (roughly) or about $2.85 pp and dues around 40¢ pp (using my purchase as a comparison). Obviously different up front costs, weeks, unit types and resorts would alter the formula. Higher point weeks would likely have a higher acquisition cost but often a lower pp dues cost. Lots of possible variables here depending on one's needs & goals. I've got to say knowing what I know if I suddenly didn't own Marriott and wanted to, I would be willing to take this gamble though I'd likely do so by building a portfolio of weeks/resorts I'd use rather than just looking at the upfront costs and fees. And in reality that's what I've done though without the knowledge at the time I purchase some of the weeks.