Forum Discussion
I'll take a fun fact from one of my previous interest threads (Community Closeness from Eco Lifestyle).
If you ever get a call to give an entrepreneur 1,000 Simoleons and give it, they may call you back to ask you for more. At this point, you don't need to give them more money, as saying that your sim can't afford it will keep the chain going. Calling them out will get you 2,000 Simoleons and ends the chain.
If you're patient enough, they'll eventually call you back to say that they got their business going off. You can either take 25,000 Simoleons or 2,500 Simoleons and a relationship gain.
So yeah, on follow-up calls, the only benefit of giving them 1,000 Simoleons more is the relationship gain.
Other than that, you only need to pay 1,000 Simoleons once (to start the chain).