Either way you go lenders want to see a track record so getting stared is surely important.

He is trying to get on track with his bills and what not but needs some support. 

Sounds like you're on the right track!

I can't see someone agreeing to sell me their house if they are only a few dollars behind on taxes, but I agree with you that it could be an indication they are delinquent on other bills.I'm just going to send to everyone and track the results.

I understand that certain websites won't track everything that happens in between.

By property, I'm looking to track cash flow by month (expected vs actual) appreciation, debt pay down, cash on cash expected vs actual, vacancy rate, etc etc.

@Talha Makki, I think @Ben Meisel is on the right track when it comes to aging and a constantly dropping price.  

This will give you more numbers to call to track down that tenant who skipped on you.  

There's little we can do to drastically change your tax position retroactively that you can't do yourself (like tracking down expenses). 

If you don't have a paycheck job and only get income from rentals, they will like to see several years track record.