The first and only measure you need to so is look at what your "competition" or the rentals you are competing against.  

I would suggest getting a handyman with you and pay him for the first few walkthroughs, say you pay him $100-200 for his time, in addition for the money, offer them to bid on your project, take notes on what needs to be done, get the units of measure needed (sq. ft of floor, sq yd of carpet, sq ft of countertop, ln ft of baseboard, etc - Use J Scotts book to get the Scope of Work).

Additionally, you included debt pay down as part of your payment. if you are going to do that I typically use an IRR measure because debt paydowns are really an investment back into the asset and not money out the door.

Then get your RE licnese and learn.. that's what I did.. then my brokers so I got paid to learn by selling RE... it was 4 to 5 years later that I first started investing but when I did I fully understood what a transaction was and is.So these class aim to shorten the learning curve.. not really reality.I have some associates though that have done very well with Paid more one on one mentoring and I have witnessed their success and they are very happy they did it and give all credit to their paid mentor.

Basically they come out, walk outside and inside, and measure the levels inside the house. 

@Keith Belzner this is a case of Ready Fire Aim, you may not ready to talk to sellers IMHO, I do appreciate the enthusiasm.Here are questions to ask the seller to SEE IF THEY ARE MOTIVATEDhttps://www.dropbox.com/s/dpnlyz7cza8bwg3/Motivate...I hope this helps.

However, as a general rule always aim to be the first-named on the insurance contract.

These properties are going to be off of homepath.com, or loopnet.com,  foreclosures, I'm looking to aim @ 2-4 units

Like, should I look on zillow for the area with the most homes for sale or recently sold or should I aim for the neighborhoods that have no activity?

I would suggest posting the scope, that will give us a good measure on which you need to take.