I'm pretty comfortable with hunting alone or with friends and have done my fair share of both. For certain types of expeditions (i.e. somewhat deeper into the woods than normal, waterfowling on larger lakes or during a more inclement period of the year) it does however seem prudent to either go with a friend or take a few extra precautions, such as advising people of where I'm going and what to do if I don't return within a reasonable time.
Unfortunately, living in the rapidly developing area of Southern Ontario, I think that it can be especially prudent to hunt with a partner in some of the county forests, crown land tracts in cottage country (especially meccas for people from Toronto) or other areas where one may come across people who are not used to or comfortable with hunting. Some people who don't understand the Trespass Act or are extremely upset by the sound of gunfire might be prone to call the police, confront you, and at times make wild claims about your behaviour. Hunting with a partner, especially when exploring new areas offers a wise insurance against having to deal with a he said/she said scenario in front of a CO or constable. If I'm hunting within an area that I know extremely well (such as all of the property lines, neighbouring cottages, many of the locals, all of the prominent geographical features, etc) I'll be less on guard and comfortable hunting alone.
From the preference stand point, I find that hunting both in groups or alone to be equally rewarding, offering differing pros and cons depending upon the locale and conditions. In any event I've lately been successful in getting a good number of friends interested enough to get their licenses in the past year or so with more to follow, so it looks as though I'll be busy enough introducing them to the sport. Especially when it comes to showing them places in increasingly developed parts of the province, I think that it's best for a new hunter to go out a couple of times with someone more experienced until they are familiar with the lay of the land, identifying game and other tricks of the trade. I get a great deal of pleasure helping others out in that manner, though I would hardly begrudge someone for taking a more solitary approach to the sport.
Regards,
Frank
PS. About a week ago I had the opportunity to fish for two day in a row all alone, and was amazed at the effect that it had on recharging my body and soul. Hunting would have had the same effect or even greater.