I know BiggerPockets already has a number of great calculators, but is there anything niche that people are interested in?

Are there any recommendations that people have on how too get organized? 

It will familiarize you with the basic terminology and benefits.

I am not sure why people purchase properties that are negatively cash-flowing. 

Sometimes people list on Airbnb but I think you're getting people who are expecting a typical vacation rental.

Your sphere doesn't know ANY older people or have relatives that own homes?

Some people love it, some people hate it.Benefit is once you get on the program the government direct deposits into your account. 

It is a 2 bed, 1 bath house, in which he is subletting to at least 3 or 4 other people.

So your super basic P&L may look like: $30,000 Rents-$3,000 insurance expense -$9,000 interest-$3,000 taxes-$8,000 operating expenses-$14,000 depreciation ----------------$7,000 loss on paper for the year  so negative taxable income But remember- $14k of that (depreciation) was something we didn't actually spend money on- so cash in bank at year end would be $7,000. 

My biggest question when I was researching all the programs was "If these people are so successful at what they do, why are they charging so much for all of this and always trying to upsell?"