To each his own for sure. I just quit staying at Hiltons due to lack of compliance for Gold. Many Hiltons (more in the US than Europe) do not comply with HH gold benefits and it is getting difficult for them to comply with the number of free Golds being given out. It is true that the guaranteed benefits for HH Gold is much more than SPG Gold and so when it is honored it is a good deal.

Anyone should be able to get a free HH Gold. On the other hand, if actually planning on stays to get HH Gold, best to stay 4 more and get SPG Platinum which is at least as good as HH Diamond for far less stays.

HH points are difficult to redeem unless you are a HH Diamond unless you plan couple of months in advance and are very flexible and possibly paying for part of the stay since rooms will not be available in a contiguous block of days.