My guess would be that if tested in court, the date the transaction was initiated by the tenant would be considered the payment date, even if it takes 3 days to post to your account.To summarize my opinion on this situation - think of it as a carrot and stick choice (like trying to get a horse to do what you want), try the carrot approach first, if that doesn't work, use the stick.

I'm hoping the refundable acts as a bit of a carrot, instead of the tenant chalking it up as a loss from day 1.

The sale pitch in the 80s and 90s was that they were buying the place, they usually didn't trash the place, at least not until they learned they had been set up to fail and lied to, if they got close enough to the carrot before the con artists declared a default, chased them off and said "next!"

@Javon Dixon I used investor carrot until recently.

I can offset this by offering the carrot of giving their entire deposit back once they're out and the place is left clean, but $900 is not enough by itself for them to find and rent a new place in such a short time.They have said they'll be paying most of July's rent on the 12th (partly why i'm meeting on the 13th).

Carrot or stick baby. 

No previous wholesaling/landlord experienceQuestion- Is it worth the $200 to start a carrot site now ($40 per month * 5 months) and start having search engines index the site along with starting to build content.

They should not be set with the intend of reaching beyond normal expectations.They are not intended to be a carrot on a stick designed to push you farther that you would realistically be able to go.

I am currently looking at Carrot and Deal Insite (Connected Investors). 

I like investor Carrot if your the only investor Carrot website in the market.