Not sure where to begin here.
I like to think you have consulted with an attorney that is versed in gambling laws and regulations. But im not sure whether you have and if you did whether you received good council.
Your are running contests that viloate the points you made...here is an example:
https://www.ludawgs.com/showthread.php?417-THURSDAY-ROCKIES-METS-DOUBLEHEADER-CONTEST
The thread above is stating people are each pledging $5 to the winner... this is clearly illegal.
The tipping concept is something I would keep to just normal posts...not contests. By involving it in these contests you are putting yourself in harms way. A judge or jury could interpret that the tipping is just the way your trying to skirt the law.
Each person who posts contests such as the one linked above is violating the law... and by you encouraging it your in violation of the law as well.
The law isn't serious when it comes to violations...office pools are illegal and are very rarely busted. But if your site does mature ... I can assure you the government will contact you...and by then you could have had 100's if not 1000's of counts
In the eyes of the law it would be deemed gambling. Here is why:
Lets say I am a bookie.... you call me and say you'd like to pledge $50 on a game... I say ok.
If you win I tip you $50 and if you lose you tip me $50
That scenario is no different than what your claiming
I know your going for the angle that its just tipping...problem it isn't you or I think... its what judges and the law will intrepret. And I can tell you that they will most likely not see it your way...for the exact reason I mentioned above.
Also you better becareful with your wall of shame. That opens yourself to libel claims...and those can be expensive
When money is changing hands between 2 or more parties relating to sports it will be deemed gambling. Such as office pools...brackets.
The way fantasy sports sites or contests sites get around it is they produce another product to justify the fee.
Pledging is no different that calling a bookie and making a wager. The money isn't changing hands at the time of the event... and you do still have the right to not pay. But in the eyes of the law its gambling.... just like your pledging will be declared
If people want to create totally free contests with no pressure they can... but pleding money is illegal in those sort of contests.
I know one of your major premises was to have tons of users pledging a buck or two in contests that could have huge pots... problem is thats illegal.
Just keep in mind the argument I made above... sit down and think about it for a bit.. I'm sure you will be able to see the dangers that courts and judges would be faced if they allowed this tipping angle to hold water 
with that challenge:
The federal law that those violate
https://www.gambling-law-us.com/Federal-Laws/sports-protection.htm
He is trying to substitute tipping for gambling.. which isn't going to work.
In previous dicussions he has mentioned that it will be great when there are thousands of users pledging a buck in contests ... the pots would be huge... which is true.
The problem is its gambling...everyone is risking money to win money from other users. Just because money doesn't change hands doesn't mean a bet isn't made.... its still a verbal contract.
He is right that nobody will need to pay... because its illegal if they do. Where he will also get in trouble is with his hall of shame. Since its illegal...if he ruins someone reputation on that and they can prove that hurt their business... he would be libel for damages
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