my score is a sad 530. I have a judgment that I am paying off, and some other small derogatory accounts (early term fees, hospital bill from having 1 child, 1 credit card from '07,student loans(none defaulted,currently in college, and a couple other things) the judgment will be paid off by the end of this year) and over the next 4 months i plan to open 2 $300 limit secured cards. and only use 30% monthly, and pay it off each month

how much improvement can i expect by jan1 2016, if any at all

Paying down what you owe now would be better then getting a secured card. No secured card will fix all those issues. 2 cards will not fix things better then 1. Forget your score until you are emplyed full time & have resonable control over all those debts. Bounce no checks & have no overdrafts. It is going to take a lot more then 1 year of on time payment history to get your score out of the hole it is in now. You are grasping at straws if you think a $300 limit is going to save you...In fact, that thinking probably has a lot to do with the score you now have. Re-think your plan.

None. Actually, your score could get worse because of opening two new cards.

First, to open a new card, you have to apply, and applying lowers your credit score for a year.

Second, right now your only card is from 2007, which means that your "average" card is over 7 years old, which is good. But if you open two new ones, which will be 0 years old, then your average card will be between 2 and 3 years old, which is bad.

Your whole premise that you can open 2 new cards and be responsible is flawed. Because opening cards, or applying them, at that rate is very irresponsible. To be responsible, you should wait more than a year between applications.

20 to 30 points maximum

It won't help much since you have so much other things wrong but it will make a place to start with getting a unsecured card.