Personally I'm not trying to worry about using superior equipment or gear at the moment. I have it set up nicely enough where I can comfortably afford my skills and skill books and properly devote the skill points to them evenly as needed. If you are having an issue with maintaining the necessary equipment then that is on you. They have clearly raised the bar on how much ISK you acquire per battle. Maybe you are over expending yourself? Purchasing skill books, or better equipment when you should be purchasing what you can afford? Which is why I have it set up where I am using all BPO (Blueprint Originals) for my single all-purpose shock trooper loadout. Then again I have enough faith my own skills to afford the luxury in knowing I will still out perform the average mercenary.

Still nonetheless you as a player/mercenary/Duster must learn to balance your accounts. Look at it like real life; if you cannot balance your own check books and money in real life well you are absolutly going to be screwed (putting it nicely) in Dust514. This is certainly something that EVE and Dust514 helps to teach better then most parents, or schools. Real life lessons in how to balance your books. Yup. Manage your assets wisely -- that is the ultimate message here.

You ask that question like you have never seen anyone ever use a credit card before. Ha-ha. Seriously this relates to real life a lot. I've seen plenty of people purchase or use higher tiered equipment they cannot properly afford soley on the basis that they believe they'll do better, and it ends up bankrupting them. Sort of a kin to your predicament. You are having trouble even staying afloat. Why? That is on you personally. It's a "you" sort of problem. I have my own path and plan and it works very well for me. I have the same bundle you do though and so do many more people. The problem with this build is that the 'Scout' is gimpy if not gimmicky this build. It's lost almost all of its frontline potential (which I had used it for) and is almost a liability in any situation outside of medium to long distance range.

If you have any of the 'Skinweave' dropsuits use them instead. I use the 'Skinweave' 'assault' class dropsuit, and do very well most rounds -- provided the match making does not throw me into an already in-progress match. Which is lame.

Now if you want to discuss whether or not the ISK also has a degredation effect this build like skil points, then discuss that. Otherwise this whole thread boils down to a "you the player" sort of problem. Is that harsh? Maybe, but then again so is New Eden, and the EVE universe. Balance your assets, and plan, plan, plan. If you are not five steps ahead on what you need or want to do then you are three steps back too far, and this game will devour you.

To answer all of your questions:

1.) The Dragonfly and Toxin suits are free - yes - but militia gear now costs per unit and the costs are rather high. My current fit is around 14,000 isk and I'm making around 90,000 - 120,000 isk a game.

2.) I am in a Corporation as can be seen beneath my name on the left, and just happen to be one of the primary squad leaders ^_^;;;

3.) I shouldn't have to get a hand-out from my corporation. What were to happen if I weren't in a corporation and were more of an introverted solo player?

4.) I don't intend to use Aurum for BPO items for two reasons. a.) because it seems pay-to-win. b.) I'm trying to simulate a player that would not normally have access to those things as not all players will invest in Aurum to play the game.

Edit: I'd imagine I would be a lot better off if I had went into one of my former specializations that I had used in previous builds as I had always had a kill-to-death ratio of above two-to-one. However, I am trying to simulate a player who isn't as skilled and thusly am going with the most difficult specialization this build has to offer which is the Close Quarters Scout build.

With this in mind, if a skilled player can't at least remain in the positives in both ISK and combat effectiveness, we can't honestly expect someone fresh to be able to do so - at this point the player would probably just quit but I've got a pretty obtuse resolve for trying to make it work xD