Ok. Thanks for all the comments. The roof is done, found a decent contractor that gave a very fair price. Looks nice, and no more water getting in.
Next concern is windows and siding. I have masonite siding now, there is some water damage on the back. I am going to replace the windows as well and have decided to do one side at a time. I have received to pieces of advice from friends, one suggests using replacement windows, the other new construction windows. I will be removing the masonite siding, fixing anything I find under it and replacing with vinyl siding. The guy that suggests NC windows, states because it is easy and it comes pre-wrapped and installed with j-channel for siding. Thoughts?
I have about 2 months worth of paying off shingles. I have decided not to borrow at all, and pay for it as I go. Using Lowes card with 0 interest for materials, and paid cash for labor. The windows and siding I am doing with some help from friends with experience.