For me it doesn't really have anything to do with how much time is between the first and second transaction - the pertinent question is "does the first transaction depend on the second?"  If the second transaction is going to be used to fund the first, its a flip I don't want to be involved in.  In your hypothetical transaction, the second transaction is used to payoff the "transactional funding" for the first one. Thus, the first transaction cannot happen without the second; the understanding being that when the second transaction funds, the proceeds are used to payoff the transactional funding for the first transaction. 

I don't find this to be irrational at all.  You wouldn't be lending for the first transaction were the second transaction not contemplated to make the proceeds available to pay it off.  Thus, the first transaction depends on the second transaction.

Best,
Robert A. Franco
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