Being new and kind of shy are two challenges that I'll have to overcome quickly in order to make real connections in the real world, face to face with other investors in my area.

I can possibly come up with 20% (extremely painfully and it would take time), but proving income will still be an issue, and I may not be able to overcome this. 

Would love to hear the boards thoughts on this.http://www.inman.com/2014/05/30/opendoor-paypal-vet-keith-rabois-big-data-house-flipping-startup-has-funding-and-will-launch-in-july/www.opendoor.comI think, if executed properly, it could work, but there are a lot of hurdles to overcome.  

Congrats @Cindy FraielliYou're in one of the few careers where you are only limited by your own ability to work hard and overcome your own self to be the best salesperson in your area.

There are many good ideas listed in the comments above for overcoming a cash shortage.

I would also like to hear about how any of you have overcome any tax, or legal hurdles (legally!).

I'm in the process of trying to raise capital which always seems to be the biggest issue to overcome.

One of the biggest objections I get from sellers is thisSeller: "yeah you sent me this letter about my property at 123 Main Street"Me: "yes thank you for responding blah blah"Seller: "so what is your offer"That seems to happen more times than not.Question 1: is the offer price in the letter a good strategyQuestion 2: if not, how do you overcome that objection from the seller

What did you do to overcome buyers' hesitations & get it sold? 

There are no amazing negotiation secrets to overcome this.Negotiation skills are about building rapport and helping an already motivated seller become comfortable with a lower price than they were initially expecting.