Let me just say that if you go ahead with your plan - by the time you finish or give up, you'll wish you had spent the $200.
Not making any judgments on your cash or spare time, but after doing this, you'll probably hate the game so much that you won't want to play it anymore.
On the technical side, with the latest launcher you can now theoretically run up to 6 clients (ie. full party) on a single machine that has the memory to handle it.
In practice, when I am multi-box farming I run 3 clients across two machines, or 2 clients across 3 machines - depending on what I am doing and what toons I need access to quickly.
Make sure the dormant clients are set to ultra low graphics, windowed mode and lowest resolution that keeps them playable. They don't need to do very much, so reduce the workload on the machine.
You then have a choice of manually controlling them or using software like IS Boxer that sends a single input to all clients on a network or computer.
The real problem you will have in DDO is coordinated movement.
Factors such as lag and different movement speeds (items, classes and enhancements) can mean not all move the same. The latter probably won't be an issue if all your toons are lvl 1 clones, but lag is still a problem.
Moving 6 toons between quests is a royal PITA. Greater bracelet of friends can mitigate this (but if you're trying to avoid spending cash, then no good), or bracelet of friends (from cards) is feasible - but you need to carry quite a few around. Ship beacons are also great where you want or need to replenish Ship buffs.
Korthos quests are good as they're all in proximity to a central point.
try to select quests where you don't need to move your 5 pikers to complete. And watch the quests that spawn mobs at the start after you've moved a certain way into the quest.
Be aware of scaling if you're going to try and run Elite quests with a single lvl 1 toon with 5 pikers. As you're on new accounts across servers, you'll start off with nada, so no pimping toons out with good gear. You could keep one toon per server to hold onto any good unbound ML0/ML1 gear for future runs.
If you're not VIP, factor in having to run on normal once and getting less favor, or having to rerun a quest 3 times to get Elite favor.
I don't do this for TP, but I do it sometimes to get some mules coin lords & Kundarak favor for extra slots. It doesn't take long to become pretty tedious.
Good luck Fiddle.