I've also learned that a sole proprietorship in Pennsylvania is not required to register a DBA.
Understand that there is a difference between a single member LLC and a sole proprietorship. With a sole proprietorship, all of your personal assets can be at risk in any legal litigation. With an LLC, which is a Limited Liability Company and not a corporation, at best your personal assets are at limited liability in any legal litigation; not very well protected on the legal front either.
So I should be good to just issue W-2's/1099's to my family members for their work in the family business? So long as this is done before the end of the year?
You can't issue *any* 2019 tax reporting documents to employees or contractors before Jan 1, 2020. So I don't know where you're getting this "before the end of the year" stuff. For 2019, W-2's and 1099-MISC's are required to be issued before Jan 31st, 2020. For 1099-MISCs, you are not required to issue those to corporations at all, regardless of how much you may have paid such an entity in 2019. You are only required to issue a 1099-MISC if you paid an individual or other unincorporated entity (such as another LLC) more than $600 during the 2019 tax year.
When your business has W-2 employees, you are required at an absolute minimum, to file IRS Form 941 at least once per quarter too. https://www.irs.gov/pub/irs-pdf/f941.pdf TurboTax does NOT provide this form for quarterly filings either. Deepening on the level of W-2 activity you have, you could be required to file the 941 monthly. So if you had W-2 employees in 2019 and did not file the 941 "at least" for each quarter you paid W-2 employees, you'll be penalized for that.
Now if you're thinking you'll get out of that just by issuing everyone a 1099-MISC, it's not quite that simple. The IRS has clear cut definitions for who is an employee, and who is a contractor. See https://www.irs.gov/newsroom/understanding-employee-vs-contractor-designation for details.
I think you'll find the cost of professional help for your first year of this well worth the cost. Doing things wrong can cost you dearly in the way of fines, penalties and back taxes. If your state taxes personal income (as PA does) then you can double those fines, penalties and back taxes. Makes the cost of professional help seem like a pittance in comparison.
