I am a debate and presentations coach, business analyst, and rhetoric/logic buff. If you'd like intelligent questions and feedback from a market, realism, or business perspective, I can certainly test the ideas hard.

Has anyone helped you with this?

I have started several entities in the USA and currently work for a startup that just raised $4m. I don't know everything about the legal system, but never paid a lawyer and have done pretty well!

You'll want to consider:
- Type of entity
- Domicile
- Are you providing services or products, physical or online?

Answers to the questions will have different ramifications such as you will still have to pay Federal taxes and taxes in states where you sell, but may avoid additional taxes from Delaware-based actions.

Happy to help if I can.

I'm a business analyst with a similar background (intelligence analysis, liberal arts, visual presentations and written reports). At my technology company we have found that SQL/DBA work can be added as you go and that "seeing the big picture" is the more essential skill.

I'd look for:
1) A tech company
2) One that is growing (see Inc 500|5000 list for too many leads to even chase)
3) Basic fluency – take some courses on codeacademy, codeschool, etc

I run a Skype coaching program for communications, speech, and debate. A few keys we have found:

1) Effective Tracking – Basically CRM, though we use a Google spreadsheet.
2) Quality Control – Internal and external monitors
3) Centralized Billing – Let the coaches coach
4) Common Feedback Repository – Scale by writing down regular comments and exercises in a way that all coaches can see

Our model works more like music lessons (e.g. $65/hr, $100/hr, etc), but we have both long- and short-term participants.

Happy to share our lessons learned.