How do I make good estimations while Analyzing a deal?

[Nate Julian]

When I bought my first property I was excited, and had my mind on doing just that for around 3 yrs. prior. I focused primarily on saving, and focused about 2% of my efforts on finding a deal. I left that up to my High School friend who happened to be a realtor. He was able to get us a pretty good deal, I'm happy with it still to this day, and learned stuff I wouldn't have otherwise without just jumping in and taking that step. I was fortunate enough to have a friend who wanted the best for me.

Going forward into my 2nd property my mindset is quite different. I want to understand it the analysis thoroughly, and make comparisons etc. I've been reading Frank Galinelli's book "What every Real Estate Investor needs to know about Cash Flow...And 36 other Key Financial Measures"

that was referred to me by @Drew Clements (thanks man!, I don't work for him, but here's the link: Frank Galinelli's Book on Amazon ) and it's helping tons!

In addition, I have added an investment property worksheet to my arsenal, but struggle with filling some of it out.

Here are a few questions I have:

1. Initial Investment
   1. Cost of Acquisition-I'm assuming that this refers to closing costs?
2. When finding current mortgage rates, what do you find easiest? Calling the bank, or lender and simply ask what they are offering up? 
   1. People talk often about shopping around for a deal with lender. If that's the case, who do you focus on calling? What types of lenders should I be looking for, and building relationships with?
3. Operating Expenses
   1. Is there an easy way to estimate expenses such as:
   1. Repairs
   2. Insurance
   3. Utilities (If necessary for owner to pay, how do you find out how much?)

Those are all of the immediate questions I have as of right now. I'm planning on meeting with a local Property Manager/Investor this week to talk more, and I'm hoping I can build the relationship with him to start understanding more about financial analysis.

Thanks for all the help! Bigger Pockets truly can be an amazing resource.