If you do get classified as a dealer (and, if you do multiple flips, you will), the calculation is identical, because the houses are inventory, and the income is ordinary income.An s-corp may be able to help with the SET.

An online system to fill out some forms will completely leave you in the dark so you will not know what you are missing out on.You sound like you are thinking long term when it comes to building credit, professional identity as a business.

I'd like for most of it (dressers/nightstands) to be identical.

It's almost identical to what my attorney told me.

Just doing some research today, units identical to mine leased out for around $895-$1075In any event, with a recent reassessment, my losses will drop to around $125 a month.  

At first he said his credit was bad because he had his identity stolen then when I later asked him about his credit he said it was bad because he owned 285 pieces of real estate before the recession hit.

The identical place across the street rented for 1500 mo.

I've already had my identity stolen once and don't want to do it again, that's why I have a really hard  time trusting websites these days (especially the "sketchy" ones you mentioned).

Lots of hassle for little benefit-the only real benefit is it hides your identity-if that really is a benefit.Generally, an LLC is Not necessary for transactional funding. 

Other times they are looking for personal information for identity theft purposes.Finally, there is a possibility this fellow is legit, but simply very new or awkward at what he does, however, my position would be the former and the latter would need to be proved before I shared any information.