Most often I have mashed and spread the pollen somewhat as I place it in contact with the stigma, but I can't offer any objective evidence that it helps or hinders fertilization; it just seems to make sense. Some pollinia are too firm to mash, and I would recommend that care be taken not to bruise or scrape the stigmatic surface with the pollen mass or whatever tool you use.
I wouldn't say its typical for actual pollination by bugs, but it doesn't seem to hurt as Paphmadman indicated.
I rarely smush pollen up much before application and rarely have a problem getting them to take.
As Eggshells noted sometimes the pollen is dry and difficult to get to adhere. I haven't tried the honey trick (yet), but just misting the stigma with a bit of water has got the job done for me. Especially for phrags.
I have some concern about using honey to make pollen stick. It is a biochemically complex and variable material of plant origin, and an international commodity that can come from virtually anywhere in the world, and is fairly commonly adulterated. There is at least some chance of carrying plant viruses, bacteria, hormones, pesticides, phytotoxins, etc. I have no doubt it is usually safe and effective for this use, and I certainly eat it, but for this use I would prefer and have used a pure glucose or sucrose syrup.