I don't think you will find any single answer to this question; it all depends on perceptions.
First of all, get expert in the area you want to invest in. I would never, ever put money into a collectible without being well versed in the subject.
If you want to generalize, you could consider desirability, demand, breadth of market, rarity, population and recent performance as good gauges of likely performance. All the first-tier HOFers like the guys you listed are always in demand and likely won't cause you to lose money over the longer term, but depending on the set at any given time you may not be able to get much of a return on the investment simply because the demand is readily filled, and you may take a haircut if you have to sell out suddenly in the teeth of a bad market. For mainstream sets like T206, I look for nice cards for the grade given (and yes, I prefer to buy them slabbed via mail--raw purchases I reserve for my visits to shows where I can handle the merch and give it a good going over) and a price that is well below where I think the card should be priced. That means being patient and scouring a lot of different venues for relative bargains. You might want to invest in a VCP scrip so you can do market comparisons on cards that interest you, just to get some idea of how they've fared over the last few years.
You also have to consider your time horizon: are you a short-term "flipper" or a long-term appreciation buyer?
I would stay away from "condition rarities" from easy sets for two reasons: (1) they have a much thinner market base--usually a few registry guys trying to build sets are what drive the market--so it may be difficult or time consuming to get your money out unless you substantially discount, and (2) if a few more cards surface in the given grade you are screwed.
I know this is contradictory to the idea of cards as investments, but buy what you genuinely enjoy owning. It makes it a lot easier to weather a market downturn when you have no problem keeping the cards because you like them.
Above all else, don't count on the investment to fuel your retirement. Pay the bills and cover your formal retirement plan first, then play with the balance in cards as a nontraditional investment.
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