Of course, we never know everything and so it becomes an easy excuse to do nothing and remain in our comfort zone.The "right moment" is now, Cynthia. 

It's too close for comfort.

I feel comfortable speaking with the owner, but have offers below his original asking price.I would like to meet him again and give him my offer that he is sure to refuse.

Getting comfortable with a Sponsor takes some research, but is a good way to set up passive streams of income and benefit from property appreciation upon sale of the asset. 

I know others do great with them, but it's not my comfort zone.  

Always consider the "worst realistic outcome" and make sure you are comfortable with that.

If you do not feel comfortable walking in that gray area, I would think about just doing a traditional rental. 

If the only reason you're paying this much is due to multiple bids and you are comfortable where you are for the next few months if needed, definitely re-evaluate during your due diligence period and exit if you find you're making a financial mistake.

For only $999.99 you can learn to flip houses in the comfort of your own home.

The IRS website says that "services of a child under age 18 aren't subject to Social Security and Medicare taxes."