A couple comments:
I would NOT advocate going dedicated healer route. It's not necessary. Spend the time you'd spend configuring a multiboxing setup with a dedicated healer on setting your team up with a repeater area or keybind set that will allow you to easily redirect all Flash of Light and Cleanse casts on the same team-mate, as well as "everyone heals themselves".
As others have mentioned, if you start taking big damage to point-blank AoE stuff.... MOVE OUT OF IT and then PAUSE DPS to heal everyone up. All too often, early on, I was suckered into thinking I needed to just burn the boss down super fast. Top everyone off, there's not a berserk timer on these heroic encounters.
To the "How do I get weapons if I'm poor". I think a good option is to run your team INDIVIDUALLY through ICC 5-man heroics for a shot at the 232 weapons that drop. In a couple hours each night, you can get a lot of your team through and probably get 1 weapon a night that way early on. When a couple of your DPS has 232s, you should be able to EASILY farm Pit of Saron Normal (first boss only) to get the rest of your team iLvl219 hammers.
My team got a complete set of 219 hammers with nothing more than green/blue quest gear and the weapons from the Amphitheatre of Anguish questline (iLvl 170-187??).
If you do decide to farm gold, I'd spend it on GDKP runs with your tank to gear it up nicely (a lot of servers run regular ToC25 GDKP runs). I spent 3000g on a couple GDKP runs with my DK and ended up with 5-6 iLvl 245 items in two weeks--- GREATLY streamlined PvE as a result.
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