You have to separate Paul Allen's personal wealth from the Blazers organization, which last I heard was not even profitable.
I have no problem with selling the naming rights, really. It's a business decision. (I think ODS changing their name to MODA was a poor choice on their part, but that's just me, and a completely separate issue). What I don't get is the idea that selling the naming rights/logo and having the result be something that doesn't make the Rose Garden look like a giant package of feminine hygiene products is necessarily mutually exclusive. They should have been able to sell out and remain proud of the result. There is making a deal to make money, and there is pimping yourself out for a buck regardless of the level of humiliation. Did they not have choices? If this were a WNBA team, I think the new logo would be fine.
I just today figured out that Moda is an insurance company. Never heard of it before and no wonder, they don't sell it in my county.