What is the best flowers to plant for reoccuring blooming...and when is the best time?

Annuals, when fertilized and dead headed will bloom continuously through the growing season - typically you plant them in the spring and they last till fall, depending on the temperature range.

They are available in a huge variety that provides an excellent choice of colours, sizes, aromas and there is a variety to fit any soil, water or light situation.

Down side is you need to replace them every year, but that is part of the fun.

Where are you. What climate? Roses are good if you're willing to prune in winter and keep them under control and deadhead them through the summer. If you deadhead, they will continue to bloom. If you don't all the plant's energy goes into seed production which is a bit of a waste since they're mainly hybrids and sterile. Plant now at the latest or get more advanced bushes to plant later. Other than that camellias are great as a shrub.

Roses

you didn't say which part of the country you live in (so I don't know which zone you live in). I suggest you request a catalog from http://www.burpee.com/ and review the catalog.