After the acquisition: There is always something to fix; learn to do it yourself. If you are not a compete bozo begin to collect a library of 'how to' books and buy good quality tools as needed. Most repairs are not rocket science but do require experience, some common sense including knowing your limitations, and having the right tool. You can always try a repair, then go to plan B and call the contractor, trying not to do additional damage in the process. When you do hire a repair guy, ask to hang out while they work and politely ask questions. If you stay out of the way, most guys will like the company and even like to explain what they are doing.
With zillo and trulia you can do your own little appraisal to help with getting the right price and the agent should be showing you comp properties as well. I think you are on the right track already by asking questions - keep it up until you understand what is going on. See if you can get a sample HUD settlement statement so you can see the typical charges, - and congratulations on entering phase II of life.