Also what kind of insurance should I request to see from the contractor?

As of now I have a solid network of laborers each with their own specialty of trades at really good prices, my partner, has been a contractor for over 30 years himself and managed many flipping properties and has a good understand about the industry.

This way you can begin building your "team" or start figuring out the best places to get loans, best contractors, etc.It's a waiting game for sure and it sucks to just sit but I'm sure everyone goes through a stagnant period in their career.Good luck out there!

Is okay, but you must have list of a lot of good contractors available

I've mentioned flipping in the past, but of course she shuts me down because we're going to lose all our money, we don't know how to fix anything ourselves, and contractors are too expensive.

I'd start locally by asking friends and family for a trusted contractor they've worked with. 

I'd like to look at the property inside and out with my contractor.

He has experience doing this type of work, we just are not cashy enough right now to have a contractor come in and do it.   

Can anyone provide recommendations on realtors, property managers and contractors in the Cleveland area?

I’m a general contractor that specializes in cabinetry and finish carpentry.