Mainly late October, literally at the last minute, while previously praising Paul Ryan for 6 months beforehand.
Advertisements, particularly tv ads, do not have a long "shelf-life" in the minds of voters, and in the fall the media becomes increasingly saturated, so it's hard for any single ad campaign to really have a serious, long-lasting effect unless they are something like an information campaign about a new scandal the target is having.
http://journals.sagepub.com/doi/abs/10.1177/1532673X09353507https://www.washingtonpost.com/news/wonk/wp/2013/01/20/political-ads-not-as-powerful-as-you-or-politicians-think/?utm_term=.03a919555255Honestly, politicians seriously need to scale back their reliance on TV advertising. I think there are enough studies now that suggest that it is mostly useless, and probably only effective if you air extensive ads running up to and during early voting/election day. Clinton's case is a good example of just lighting money on fire. Even if her ad campaign bought her 1-3 points in votes at some point in October, the Comey letter probably destroyed that by turning the people she convinced via ads against her again. Point is: Maybe ads get you some support, but minor or major late-breaking revelations can take it away almost instantly.
Personally I'd rather see the party invest many millions in constant year-round organizing
(in rural/exurban areas as well), instead of parachuting in during elections only.