What obstacles did you over come along the way, creatively?

Having deals under my belt was all I needed to overcome the age obstacle because now I could talk about the deals I've done and that immediately gets past the "who do you think you are, kid?"

I encourage you, if you haven't already done so, to apply his overcoming objections/complaints techniques and rebuttals, or listen to @Michael Quarles podcasts/youtube...he has some great content and live calls talking to sellers. 

Can't offer much advice on how to overcome the lack of confidence but as a guy that grew up with a mom that suffered from the same issues I just want to say it sounds like you're pointed in the right direction. 

Which is most likely why the agent hasn't gotten to it yet (It is really an exercise in futility often especially if there is over 50K to overcome).

Overall I think it's a tough hurdle to overcome, but you can do it! 

I'm here near Bukit Timah.I'm currently trying to overcome my analysis paralysis phase and have been diligently preparing to start my investing in 2015.

Writing a book on notes has a lot of variables to overcome.

One way to overcome this is to partner with someone who IS more knowledgeable.

Typically the only one of these objections we can overcome is the last.