Surround yourself with successful motivated people and your fear of failure will diminish (never went away for me, but I'm able to manage it).

Questions 1)  ultimately is the goal to have your properties paid off to increase the cash flow, or it is better to use more leverage to build up the portfolio eventhough the total cash flow could diminish? 

I'd just come out and tell her that you want to do business but feel it's important that she gets a third party involved as you want to avoid the perception that you took advantage of her in some way due to her diminished capacity.

One wrong move and you can be on the hook for more than you expect, diminishing your returns and lessening the cash on hand to invest.

Feel free to reach out and I'll shoot you his contact - accuracy is slightly diminished from his normal data (response rates around 21% for text instead of usual 30%ish), I'm guessing this is because often times the owners are busier than everyday people or less willing to sell if its an investment property in their company. 

I personally think if it is going to be your personal home and you are currently renting the necessity to make every penny possible diminishes.

During great markets there are good and bad deals and during downturns there are good and bad dealsDuring an upmarket mistakes can be diminished due to appreciation in a property and magnified in a down market, but if you try and “play the market” you will not winYou also didn’t mention type of investing you want to do?

This is precisely what has happened and your property rights have been diminished as a result.   

Your cash-on-cash return diminishes as your down payment increases.

There is a diminishing returns all things being equal.