I agree that she shouldn't give up acting. She has improved tremendously over the years.
As I mentioned before, I would love for her to find a role as a supporting character in an ensemble comedy movie.
If I had to make a time line, it'd be:
May
- Return to the studio
- Return to working out either at the gym or home, whatevs.
- Shoot a spread for People magazine with Luca and Mike.
June
- People magazine cover w/Hilary and her son is released.
August
- Shoot a guest starring role on a major network show.
- At the same time, her PR people announce a supporting role in a major motion picture.
September
- Hilary begins shopping a nearly completed record to labels.
October
- Guest spot premieres
- Record deal secured
- Shoots her scenes in two-three weeks for the movie.
November
- Announces her new label
- Returns to the studio to record new tracks
- Shoots February issue of Maxim/Elle/something high fashion.
December
- Hilary premieres a new track on official website just in time for the holidays. Free for a limited time (two weeks).
- iTunes release of new track in late December.
January
- Issue of Maxim/Elle/high fashion is released with in-depth interview.
- Another guest appearance is shot for February sweeps.
February
- Completes 4th studio album
- Guest spot premieres
March
- First official single premieres at the end of the month.
- Shoots a bunch of magazine spreads.
April
- Radio promo tour
May
- New movie comes out with 2-3 promotional appearances from Hilary.
- Embarks on a 10-date club tour promoting the album
June
- First week of June album release
- Promotional blitz (I'm talking at least 6 TV appearances including an in-depth interview with one of the old ladies who does those & a handful of radio interviews, magazine covers, etc)
- UK promo
Doesn't sound too unrealistic, I know.
Keep in mind I just came up with all of that in the last 15-20 minutes so be prepared for grammatical errors, etc.
The Most Wanted tour & SMWT were massive. Dignity did well too regardless of what people said. 
