I think you first need to check out what channels are offered by each service and what the price points are (ex. you want Home and Garden channel, one service includes it in their base package but another requires a higher package that's too much for you to pay).
If cable has what you want and a price you can afford I'd say to give them a shot first. Reason is that there is no 1 or 2 year commitment with cable, so if you don't like them you can walk away and try something else. Cable also offers local channels (like in Chicago you can get CLTV, a local news channel) which D* and E* don't carry. Also many folks do not like that they loose the local weather forcast on satellite, you just get a generic national forcast. And you can also get a digital video recorder from cable (usually), it's not a Tivo for for many it's good enough.
Onto satellite. The comment about DBS going out with heavy cloud cover, there's something wrong with their setup then, if the dish is properly aimed it should go out only during periods of heavy rains. Folks in hurricane areas reported that they didn't loose their signal once durning some of the storms they had. My will go out during heavy downpours and if snow builds up on the dish, that's why mine is ground mounted so I can just go out and brush the snow off. Also, some homeowners associations will say you can't put up a dish, their usually wrong. The FCC has a law that says that unless there's some specific reason, such as placement would cause a safety concern or it's an historic building, that they can't stop you from putting a dish up.
As for which service, I've had DirecTV (D*), gave Dish (E*) a try and went back to D*. I liked the channels offered by E* but the E* 'high end' hardware when it first comes out tends to have a bunch of bugs, give them a year and it settles down. You might want to check out
www.satelliteguys.us and
www.dbstalk.com for what folks say about both services and the receivers you're thinking about buying. Good luck!