@Jada Walker The money spent on an inspector will be some of the best you spend. Be sure to get one that comes recommended. The best ones are ex-contractors/people who used to work in the trades and are now do this in a semi-retired capacity. Others have never really worked on buildings in their life. Many inspectors are totally fine if you walk the house with them and are trying to learn what they're looking for/at. Their report will give you a decent idea of problem areas. But there are limitations to where they will and can look. Having the report ready and sharing it with a contractor who then walks the house for scope-of-work will give you a more thorough understanding of what is wrong and, most importantly, what it could cost you. Even still, pay them something for their time and get several bids for the work. You will likely be shocked at how different the prices can be. Do you know anyone who is a general contractor by chance? Maybe they'd be willing to help out and give you notes as a friend.
A building is a complete system that works together. To find points of failure can be a challenge. General contractors are contractors certified to work and have knowledge in most all aspects of that system, unlike other contractors who can have very specific concentrations and knowledge bases. But it is important to bring in that knowledge of the complete system. Because things can look fine and not be. Things can look awful and not be. For example, a roof can have discoloration and stains from a variety of causes. Some to worry about and others not. It's a big price tag... I guess all I'm saying is short of pulling up and seeing tarps all across the roof I would get a professional opinion on cost. Your specific REI strategy comes into play too on what you will be putting money into and where else it would be better spent.
But hiring an inspector and walking the property with them will help you a lot. The more you join in these conversations with the people you come to work with, the more you will end up absorbing. Good luck with your search!