Bring confidence, excitement and motivation and anyone would be a fool to not want you on the team! 

If not sure or not confident, I would pay a professional.

utm_source=search&utm_medium=internal&utm_campaign=books (books recommended by BPers)Also, you can review the quick links below to help solidify your grip on this site. http://www.biggerpockets.com/startherehttp://www.biggerpockets.com/meethttps://www.biggerpockets.com/alertsHow to Use @Mentions on BiggerPocketshttps://www.biggerpockets.com/ruleshttps://www.biggerpockets.com/termshttps://www.biggerpockets.com/inviteshttps://www.biggerpockets.com/perkshttps://www.biggerpockets.com/forums/categorieshttps://www.biggerpockets.com/courses/a-beginners-introduction-to-real-estate-investing (video courses)https://www.biggerpockets.com/real-estate-investing (Ultimate beginner's guide to REI)After becoming more knowledgeable and confident take action to snag your first real estate investment deal.Here are some solid tips before buying your 1st investment propertyhttps://www.biggerpockets.com/renewsblog/2014/12/19/real-estate-investing-success-smart-tips/Don't get caught up in analysis paralysis.Take calculated risks if needed and you shall be rewarded!"

They tend to foster harmonious relationships with the tenants by getting to know them and their situation. 

You have to become more confident and not allow anyone to guilt or shame you.

I hope to find a mentor that can help move me into that direction while utilizing the experience and benefits of the partnerships I have built in Chicago and other States.MY motto is to "Build Dreams Fostering Hope" for I realize that each dream that is accomplished is based in the hope that preceded it!!  

More than anything,  I wanted to get a second opinion so that I could confidently tell my friend that I did it.

5) Ideas on how to best gain the confidence of a prospective private money lender?

This gives me confidence and the credibility when talking to people about real estate.

Thanks @Jay Hinrichs for the vote of confidence on the crash pad niche idea.I don't remember how I originally stumbled across BP, but I am glad I did.