Not sure of how my mother's eventual passing, will change that, but I anticipate that he might feel that her passing eliminates the need to generate income from that unit, and he can resume a rent free status.

What programs/websites do you use to track your portfolio and/or net worth?

There are many options and taking cash from one of the buildings that is generating income is definitely an option provided it is not in an LLC, Corp. or any other structure that would make this co-mingling of funds. 

What are the pros and cons of buying properties at auction from auction websites like xome.com?

My main objective is to generate $15k of reliable, monthly cashflow in the next 5-6 years with a buy and hold investment strategy.

I wanted to know if I could pull a HELOC to invest that money into purchasing another property where I could generate passive income.

Or do improvements not even matter that much since most of the appraisal value will be based on the income the property generates? 

First one is a basic intro (we buy houses, want to buy 2 in your town this spring, selling direct is great for X reasons, let me know if you want an offer), second one highlights what type of sellers typically like to sell to investors (own timeline, no hassle, house needs repairs etc), third mailing is a simple postcard that has similar message on it, fourth mailing is a letter saying I've reached out before and thought you might find these FAQs useful (and I include a 4 pg FAQ distilled from my website)-- I expected that letter to have more response (you'll see above the 4th mailing had a <1% response rate) and it may be that ppl are waiting til after Easter to call, as I get more calls after holidays when ppl have had time to talk to their family.How to track all of this... you can guess by now that I'm super data oriented.

There are IRA and other designated IRA that can bring down your AGI.  2)If you make way over 150k, than I would suggest investing in a diversified property group with different outcomes (some rentals might not have a good future appreciation or in a bad area, but have a good cash flow that will absorb your other rental loss ). 3) Invest in other business as a passive investor where you can generate passive income.

I would have no problem to add the extra cash if they dont want to negotiate, and if I feel like I really want the house.2) i see in this website people hoping that the houses they are trying to buy appraise at the offered price.