After uninstalling and reinstalling LR 5.5 AND Photoshop CC (2014) I was finally able to get images to go from LR to PS, but after editing the TIFs are not reimporting into Lightroom. The images save in the same folder.
OS Windows 7 Pro 64-bit
Lightroom Version 5.5
Photoshop Version: Photoshop CC (2014)
Intel Core i7 2.4ghz