1040s, 1099s, Schedule Cs, lost of confusion & 4 years behind... HELP?

You are looking for a "straight answer" to about 15 basic questions (which you have phrased in a bunch of convoluted statements, assumptions, and queries).

There are several IRS publications, easily found at the

Since you said you don't know what to look for, but are able to "fill [forms] out on my own [...] by looking up terms and definitions as I go. ", try this:

Since the tax laws have changed every year since the last time you filed, you should expect to pay some kind of price for the services of someone (or some software) who can help you with each and every missing year. To expect detailed free help with each of your tax returns and schedules for multiple past-due years is not very realistic, but perhaps there are some Good Samaritans here.

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Form 1040 is needed in the years you have any schedules not supported by a

Schedule C is where you would report your income from self-employment (refered to as IC jobs) and claim your business expenses. You will need to be able to support the claimed expenses, so if possible reconstruct them from other records or get statements from the people you spent money with. You may also need Schedule SE (self-employment tax), Form 8829 (home office), and a 4562 (depreciation of that laptop), among other possible forms or schedules.

Business expenses are taken on Schedule C, as mentioned above. Unreimbursed employee business expenses, like from your "regular job", get claimed on Form 2106 which flows to Schedule A and subjected to a 2% of AGI floor, which often times means they are not deductible.

State laws vary, and I'm not familiar enough with IL to know what specific forms they have. Georgia does not have separate reporting for the Schedule C, A, etc, but Alabama does. Maybe someone can give you more spcific info on what IL tax reporting requirements are.

You only need money if you expect someone else to dig you out of your hole.

There won't be any simple answers because tax laws vary, individual facts and circumstances vary, and state laws vary.

If you have specific questions, more than likely someone here will be willing to answer them for you. Best if you ask them one at a time.

More than likely the transcripts won't have any state withholding. So for the W-2 data, contact the former employers to get copies of the W-2 so you have state and local withholding numbers.