I just saw the movie again on the Flix channel and I was immediately wondering if Rocky managed to get his financial situation under control. It seems like here, Rocky Balboa while not as hard off as he was in the fifth movie, is none the less, trying to live rather frugal and within his own means.

or b) you make a living from endorsing products (which he was probably put off after Rocky 2).
He was doing that successfuly in Rocky III

that theory is complete bs
we see him loose the money in rocky v so that is the only possible explanation

Since according to ESPN Sylvester Stallone acts as if Rocky V never happened, here's what I think happened to Rocky's fortune:
Sometime around 1995 the Balboa's go bankrupt, not because Paulie gave power of attorney to their accountant, but because Rocky hadn't boxed in years and they spent millions of dollars on clothes, cars, etc. And they owed millions in back taxes. So after selling everything they owned they only had enough to buy a small house in their old neighborhood in Philadelphia and open a restaurant (according to the production designer for "Rocky Balboa" Rocky and Adridan moved into the house sometime in the mid to late 90s). I also think Robert was given some sort of trust that couldn't be touched by the IRS, otherwise he wouldn't have been able to quit his job as a corporate employee.

Assuming, for the sake of argument, that Rocky 5 is indeed ignoredhe still hasn't boxed for a while and had no other obvious source of income. His wife's medical bills would've been big. So would his son's education (I'm assuming he went to some illustrious college and Uni to get the start in life his dad never had). Lamborghinis cost a lot to run and maintain. Same goes for big houses.
If you're a bestselling singer or writer, your royalties can keep you rich for years after you retire. For sportsmen, it's not the same. Either a) you become a pundit (can't see Balboa as a professional talker) or b) you make a living from endorsing products (which he was probably put off after Rocky 2).
I can quite easily see his fortune being whittled down over 21 years from 1985 to 2006.
Rocky Balboa lives for the applause

This ignores how many superstar athlete restaurants have failed.

i guarantee you that a resteraunt ran by a former heavyweight champion of the wold would bring in millions

He hit rock bottom (no pun intended) financially in ROCKY V. Many years later looks like he was worked himself up to middle class at least but not rich. That restraint helped him a bit. realistically his image and superstar figure of being a legendary fighter would give him enough to live well anyday. Example: Michael Jordan does not have to work another day of his life just his legend himself will give him a million or more a day.

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Sylvester Stallone's explanation regarding the brain damage:
"When Rocky was diagnosed with brain damage, it must be noted that many athletes have a form of brain damage including football players, soccer players, and other individuals in contact sports such as rugby, etc. Rocky never went for a second opinion and yielded to his wife's wishes to stop. So with the advent of new research techniques into brain damage, Rocky was found to be normal among fighters, and he was suffering the results of a severe concussion. By today's standards Rocky Balboa would be given a clean bill of health for fighters."
Source:
http://www.aintitcool.com/node/30861

Rocky's brain inury went the same place his eye injury went between Rocky II and Rocky III.

Stallone didn't direct Rocky V.
Some days, you just can't get rid of a bomb.

In the "Rocky Saga" documentary, his brother, Frank, implies that Sly was doing other things like golfing. Perhaps, he didn't put as much effort into it as when he is directing. There is also the "Rocky dies at the end" script. Perhaps, if he would have directed it, he would have gone that route to give the saga its final, brutal punch, although that would have been really sad. He should have instead discussed the movie's strengths.

@Balboasaurus
he had no choice but to acknowledge the events of Rocky V.
Except for Rocky's brain injury, which miraculously vanishes in this movie.
As for why Stallone bashed
Rocky 5
, I think it's because everybody else bashed it so he had to go along with them, regardless of his opinion. It's not like he's gonna go, "You're all wrong,
Rocky 5
's a masterpiece."

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Not only is Rocky's financial situation a direct result of Rocky V, we also get another reference with the "home team" line which was established in V.

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Rambo III better than First Blood? Yeah, your opinion shouldn't be outlawed.
George Orwell was an optimist.

Rocky 5 better than 6? Your opinion is illegal.

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Oh, I see. I went on rambling about Robert.
If he really wanted to give Rocky a proper send off, he had no choice but to acknowledge the events of Rocky V. I also never understood why he would bash Rocky V; he wrote it.

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What do you mean Lonestarr when you say that the film totally ignores the events in Rocky V, but that it is a direct continuation of it? Color me confused.
I think both Rocky and Robert were living under the shadow of the former. We saw a bit of that in Rocky V when the neighbors at the bar mock him for losing his money. Then Robert tried to train with Uncle Paulie to fight off the bully Maybe, at some point after Rocky V, he wanted to be like his dad, but then decided to go to college instead, but wasn't happy with the field he chose to study. I wonder if he met people who challenged him to sparring matches, and he got tired of it.
Another theory of mine is that their relationship became strained after Adrian's passing because Rocky kept living in the past.
just some thoughts