Does anyone know of a good software program to track my expenses?

Make sure the taxes are not based on some program. 

Impossible to say without knowing the loan program, and lenders have overlays, but 6 months of payments (PITI) is a good ballpark rule of thumb.

When someone asks if the we take Section 8 the correct answer is that we "take in to account all sources of income however the unit has not been inspected to be included with the Section 8 program". 

We are interested in purchasing a vacation rental and immediately participating in a rental program.

I am sure you have read if you obtain an FHA mortgage your minimum down payment on 1-4 units owner occupied remains at 3.5%, however with conventional more than one unit you would be looking at anywhere from 5-20% down (depending on programs in your area). 

Please be prepared for a ton of questions.

You'd be surprised at how few sponsors provide this, even though its not difficult to prepare.

Opioids from Johns Hopkins and the University of Maryland Medical Center continue to flood the poorest of neighborhoods, leaving the African American communities in a perpetual state of addiction, along with the need for constant government assistance programs.

there are other lending programs that would not require this but if you are wanting the best programs agency debt then @Janelle Groenhout has the right idea