I like Alcoa/Mastic or Certainteed/Wolverine vinyl siding. They have always stood behind their products when ever I needed them to. Note* It was not that often because their quality is pretty consistant.
I have Wolverine Benchmark on my home.
You need to look for the profiles that you like and as long as you choose a thickness of around .044, and a lighter color, you should be in good shape!
I would stay away from any siding that has a photo finish applied to it.
Now, as far wraping your trim, I did mine and I highly recommend it. Why spill paint on your new vinyl while trying to paint your trim? Make sure that the fascia is bent to go under your drip edge or shingles.
You should go to the Vinyl Siding Institute website, (I'm sorry, I'm going to have to write it down on the front of my PC), do a search and it's there.
You will be able to do the research on the different manufactures and products they offer. You should look at the accessories that can really dress up a house for short money.
You can also go to www.harveyind.com to look up vinyl siding as well as a wide selection of products like windows and doors.
Alcoa and Certainteed both offer a wide assortment to choose from. Also Mount Master products like light blocks, and gable vents are a nice touch. Vinyl shutters and seamless aluminum gutters add the final dressing and leaves you with a home that you will be proud of and maintaince free for a long time.
Final note* If you are hiring this work out, find an old established company, get references and a insurance certificate. Make sure that all warrantys and guarantees are in your contract.