Actually, what Anshultz did was pretty smart - for him...

Rio Grande was a very conservatively managed railroad which had large cash reserves set aside for business downturns, modernization, and the like. I don't recall the exact amount of cash that was on hand, but recall that when Anshultz gained control of the railroad, he was able to recapitalize the railroad (i.e. take on more debt and do a special distribution) which essentially paid off his investment.

The Southern Pacific acquisition wasn't nearly as much fun. With the UP purchasing WP, D&RGW lost their primary western connection. SP was in a major world of hurt as the overland route was their primary business outside of chemicals in the south. The merger between the two basically became a defensive maneuver, bolstered by the fact that SP was cheap given business conditions. SP getting blown out of the SFSP merger didn't help matters either.

The main issue with SP though was that their business wasn't particularly strong, they had very strong competition from Santa Fe to the south, and UP wasn't taking prisoners. At this point, either Anshultz was very smart and took the long view (UP had to come a calling sometime or other) or just lucky.

Against that backdrop, I think Anshultz's business strategy was to conservatively maintain the business without investing much of his own money. Some locomotives were leased, some tracks moved around, and branches were sold off but there was nothing like was happening on the other western lines.

Culturally the D&RGW was a fairly hungry outfit, thanks to several bankruptcies in it's formulative years, struggled with boom bust mining cycles, and ran a lean organization. SP was far more successful early in life, and seemed not to have that same bootstrap mentality.

Anyhow, that's my perspective. In short, either Anshultz was a strong forward thinker, or he was lucky as heck. Either way, he didn't lose money with his investment, and ended up becoming a major stockholder in the UP.