Well, dislike of idea of buying points is based on whatever is most important to you. If it's dollars ONLY, then, don't do it. Many of us points owners do it for other reasons. After all, if the ONLY criteria for buying a car was price, who would ever buy an expensive sportscar? I believe only you can answer your own question based on the pros and cons you have learned about. What I would do doesn't matter much (or shouldn't). But still.... There is very little benefit for charimans level, I would definitely *not* do it for that. It's a non factor to me. So, it is a CON to me just as you have it. However, presidential does have a lot of tangible benefits, so, would be a PRO if you changed your request to presidential.
Another PRO would be avoiding various fees such as lockoff, MVCI trading in II, another II account. Those would be extra fees as they are now when you are not enrolled. Another PRO is what has happened with enrolled weeks owner and the virus, more options with all these pandemic issues such as free retrades.
I would point out on your renting points claim that some here really don't trust or like renting from others (I would never ever do it myself). If that doesn't bother you, keep it on your CON list.
Your #2 CON, is fine during non pandemic years, but, wasn't so great a deal for those renters out there this year. Kind of hurt bad in some cases.
Obvious PRO is flexibility, part week reservations, saving on airfares, etc. But that may not mean much to you.