Hi @Michelle Kline - I wish I had a good answer to this question! I can tell you how we have made progress in this area - learning through trial and error. We put a lot of sweat equity into our primary residence and our first rental property. Biggest lesson I learned was to double my estimates for time and cost!
On our current project, we are paying a contractor (more of handyman) to do almost all of the work. He has been invaluable with helping to plan things out and answer questions! He knows the problems we will run into before we get there. I now understand why you hire a (good) general contractor and am so much more willing to pay those prices. The work gets done in the right order, with the right amount of planning, and so much faster (we work full time day jobs). If it's within the budget, I would try to find someone who can be your GC!
Finding a good contractor is a whole other topic that I don't have much experience with. In the current example, I seemed to have lucked out and found someone on craigslist. I interviewed his references and just had to try and give my best judge of character... until meeting him, I didn't think I could find someone who communicated well... but they are out there!
