Independent contractor vs company driver

Since the Swift incident left me unemployed, none of the major companies I spoke with will bring me on (even after being honest about what happened, Swift is still giving details about the incident leading to termination, which I believe is the willfull release of confidential information, but that's another issue); I decided to take an offer as an independent contractor for a local carrier with the mindset that I will revisit the issue and explore options at the 6 and/or 12 month point to see if I can return to company driver status with a major carrier, since I am concerned with health insurance (as an independent contractor, most of those expenses I would be responsible for).

My questions are:

How do I document out of pocket expenses for either reimbursement or tax reporting purposes? What is allowable as deductible?

How much of salary is a safe percentage to set aside for income tax purposes?

Does anyone know of any good medical/dental program that will allow me to get care wherever I may be, even if it is not home?

 

I am not looking to be an IC for more than 6-12 months, just to get the 'stank' off of me.....

I am thinking 10% of my income should be good to start with. For 2015, I will only have unemployment income from 1/15 - 8/15 (non taxable), employment income from Swift 8/15 - 11/15 (taxable, but withheld at the max amount) and whatever I get in the month of December.

 

1099; but I plan on looking at my options at the 6-8 month mark.

 

This particular employer is going to take $1500 as a deposit (15 payments of $100) to cover the deductible for any at-fault claims. refundable upon separation if no claims are paid. It sucks; which is part of the reason I want to limit my tenure to 6-12 months.