QuickBooks is not intuitive, and it'll take some time to set it up.

You know him better, so use your intuition to determine the best way to have this conversation.Silly question, and maybe I am just naive, but don't most contractors bake these admin/reimbursement costs into their total quote?

I have looked at Quickbooks, and find Quicken for user more user-friendly and intuitive. 

•Imagine having real-time price per square foot data at your fingertips, visualized through an intuitive heatmap.

Here're some online calculators: from Intuit/TurboTax, from H&R Block, from NerdWallet, from TaxAct, and you can find dozens more online.

@Sree Todu,Your intuitions are dead right -- if you carry a note from your sale, the face value of that note is not automatically deferred with the 1031 exchange.  

It's counter intuitive however, we find this approach to be highly effective. 

Overtime, you will start to develop an intuition of price very quickly.  

If you are married, try leveraging your wife's intuition on this a bit.I like to be within an hour or so of our properties so that I can manage them easily myself.

You have to decide on your criteria and then run a pro forma analysis on each property to determine if it meets your metrics.Once you do that 50 or 100 times, you'll start to see patterns and will know intuitively if a deal might work for you.BP has a great book on investing in rental properties by Brandon Turner.