Will what I'm doing get me where I want to be?

Personally, I think you may be over-thinking this?

In terms of the first part of your question, you wanted to know if you should just lose fat, or gain muscle and lose fat. The percentages and weights you listed are basically meaningless in my opinion. Isn't what matters whether or not you're happy with the way your body looks? For example, are you happy with the amount of muscle you have? If so, then just continue to lose fat to reach your goal. If after looking at yourself you do want to add some muscle mass right now, your best bet is to rethink the 1400 calories a day diet. Keep in mind that you can always adjust things as you go.

Remember, as a newbie lifter with excess fat, you CAN add both add muscle and lose fat at the same time on a restricted calorie intake, but this ability will really slow down as you get closer to your goal. At some point (probably really soon), you're going to have to pick one or the other. Yes, if everything were spot on in terms of diet and exercise, you might be able to both add mass and lose fat, but you're also probably not going to do that in the time you've selected.

Either way, at some point, you're going to have to up the calories. You're just not going to continue to add mass eating 1400 calories a day.

I suppose overall, I'm thinking if what you've been doing is working, why not continue to do that until it stops working? No one is going to be able to tell you "do this exact thing" and you'll make it to your ideal body. This is all trial and error. In addition, as you body adapts to both diet and exercise, you have to change things up to reach the kind of fitness you're seeking.

TL:DR; do what works till it doesn't, then try something else.

Okay, I think I have a decent idea of what I need to do. I don't really have the money right now to add too many weights or get the cycle ops, even one of the cheaper ones. For now, it looks like I'll have to continue doing close to what I'm doing because of time, money and Alaska weather, but I'll definitely see what I can do about adding more weight. I'll be able to add more time in May when school is done. And when the snow falls in again in October, I should be in a better position to incorporate more of the other stuff when I have to come back indoors.

Here's to warmer weather coming your way and all the best on your continued exercise. I think just increasing the intensity and duration of what you are already doing may take you to the next level (just make sure to eat enough calories to support it). Fire up that furnace and watch things melt (including the Alaska winter). ;-]