Just spent some time digging through closed-end fund opportunities from 2023, and honestly there's something worth revisiting here about dividend increases and income strategies that still holds lessons for portfolio building.

Back then the market was pricing in some interesting setups. The core idea was simple: three CEFs could hand you a 10.5% yield without needing massive capital. What caught my attention was how different these funds approached monthly payouts - that's the real difference from regular stocks where you're waiting three months between dividends.

PIMCO's Dynamic Income Fund (PDI) was yielding 13.3% at the time, and the thing about PIMCO is they've got serious pedigree in the bond space. Their track record showed PDI matching the S&P 500's 8% annualized returns over a decade, which for a bond fund is genuinely rare. What made it interesting wasn't just the yield - it was that investors were actually getting their returns in cash rather than chasing paper gains. The fund also had a history of special dividends on top of regular payouts, with the regular dividend itself growing 25% over that ten-year stretch.

Then there was Liberty All-Star Equity Fund (USA), sitting at 9.7% yield and holding the kind of stocks everyone recognizes - Alphabet, Microsoft, Visa, that tier of holdings. It was returning 12% annualized, which speaks to solid management. The catch with USA was that dividend fluctuates with net asset value, so it wasn't for people wanting predictable monthly income. But that flexibility let management keep capital deployed without cutting dividends.

The third pick was Cohen & Steers Real Estate Opportunities Fund (RLTY) at 8.4%, focused on large-cap REITs like Prologis and American Tower. Being relatively new meant it was trading at a discount, which historically has been the best signal for CEF entry points.

The broader lesson about dividend increases in 2023 and beyond: CEF discounts to net asset value matter more than most people realize. When you catch funds trading below their actual holdings value, you're essentially buying future gains on top of the yield. That's the real edge. The funds showing the biggest dividend increases typically had management teams that weren't afraid to deploy capital aggressively while maintaining shareholder payouts. Worth keeping that framework in mind when evaluating income strategies now.