When retainers win games, do they receive gifts? Also, if you are gifting someone a retainer, can they have paths or must they be a completely from scratch character?
Hmm… I doubt it. If you have Retainers who can get Gifts, then you would, in essence, be getting multiple Gifts in one Game.
What about starting them out with a path or two? They seem like somewhat weak gifts otherwise.
That still makes them rather powerful, perhaps at higher levels, maybe. But the real purpose of retainers is mainly for non-combat style characters to have characters who complement their skill set, rather than someone who is equivalently powerful. From that stand point, its quite a nice gift to have. Keep in mind also, that each retainer gets 5XP per game, win or lose. That is virtually raising the XP you get per game, since you can sink that into things that you would like to have, but that don't help you directly.
For example, a politician character obviously is going to put a lot of points into non combat skills, that is their area of expertise. This makes them extremely vulnerable to monsters, though. Now for the price of a single gift, or perhaps 7XP if they decide to do it that way, they get a minion who can be perfectly specialized in combat. It not only gives you a second set of hands, but since (as I recall) you build the retainer yourself, you get someone who can be extremely skilled at what he does, filling a wide variety of niches.
No gifts for retainers has been a long standing rule, as far as I know.
Think of Batman's butler. He is not, and never will be, a superhero. But he is someone Batman can trust to take care of things, and that is quite valuable in and of itself. Retainers are like that. They're normal people that the PC can trust. They might be quite good at whatever they do, but they are just normal people.
That doesn't necessarily mean that they couldn't learn a path, but I would say they can't start out with one. The rules in Vampire The Masquerade for teaching disciplines to ghouls might be a useful starting point. I don't recall the specifics, or even what book you'd want to look at, but the executive summary is:
it costs more XP
they're capped at a lower rating
they have a much smaller pool to power the ability with
there are some things it's just not possible to teach them
The exception is if you can get someone else to play the retainer as a PC. Then they get gifts, paths, XP, etc. the same as any other High Roller. This has been done before, and can create some interesting character dynamics.
In certain rare cases people have acquired Retainers that have powers. It is typically a High-Seasoned/Vet sort of thing. The uses of even a mortal retainer are nigh-endless, however. One PC was awarded 3 Retainers at the less optimal build common to Mortals, & used them to great effect.
But it is acceptable as a gift to a high-seasoned character?
If allowed complete freedom in design & background, certainly. Bear in mind you run them, not the GM.