I start out expecting to get the room I reserved. I very often get upgraded, but since I wasn't expecting it to begin with, I'm always happy with what I get. I know that I will have access to the lounge no matter what and that is one of the nicest perks at some hotels.
I don't really need a suite most of the time. Even if I'm staying a week somewhere, I don't spend that much time in the room. The suites were most useful when my kids were younger the couple of times a year I had my family with me. Now that my kids are both in college, I get a second room anyhow, usually with points. If I'm vacationing somewhere, late check-out and perhaps free breakfast in a lounge are more important than a bigger room. I'm there to see the sights, not to spend time in a suite.
The program is "based upon availability" so I don't know why I've seen some people demand that they must absolutely get something better and are furious if the hotel is full and nothing is available other than what they reserved and are paying for. No sense in setting yourself up for disappointment. The PFL program is a very nice perk if you go in with the right expectations.
5* is also pretty nice if you don't start out with a sense of entitlement. The staff will generally try to help you but sometimes it's just not possible if a property is full. Most of the time it does make a difference, though. I've gotten 1BR units instead of studios at WKORV and they do try to be accommodating regarding room requests. My flight usually leaves around 5 pm so late checkout at noon is very useful to me too. The option to wait until October 1 to convert to Starpoints and get an extra 10% of those points is good too. I do value Starpoints enough that I don't feel I'm losing much compared to renting. Renting is better, but if for some reason I haven't found a renter and I don't want to deal with it anymore, the Starpoints will bring me enough value that I don't regret converting. The conversion provides just a little more flexibility to my ownership.
Is 5* worth a lot of money - probably not, especially in a strictly financial sense. Does it make my vacations a little nicer? Definitely. It is a luxury item, like anything else you might splurge on. The number of weeks I own in Hawaii cost me what a lake house would have cost in a more remote part of the state. I enjoy my Hawaii trips much more and I spend as much time there as I would in any other full time ownership real estate, without maintenance hassles. I can't get my money back, but I have no interest in selling anyhow. I couldn't get anything similar to what I have in Hawaii for the money I spent. Kath is doing it for a whole lot less, so it's even better!