HOLLY--call a couple roofing companies and ask them to come give you an estimate. I would be surprised if they charge for that. Depending on the quality of the roofing shingles, weather, support underneath them,'etc. A roof can last from 15-25 years. Depending on how many layers of shingles are already on the roof you can put a new layer on or you have to rip it all off and start fresh. If the plywood base is spongy you are going to want to have that fixed.
I suspect the estimater would climb in the attic and maybe on the roof itself. Once you have a couple quotes ask for recommendations, check the Better Business Bureau for complaints or compliments.
Ask about payment plans from the company and at your mortgage bank ask about a Home Improvement Loan.
You might also ask each estimater about the bathroom ceiling repair. They may not be able to do it, but maybe they can.
Lowe's, Menards, etc may be able to recommend some companies for you to contact.