If I'm flipping, my discount needs to be deep to create a spread. 

If they work independently, set their schedule, and use their resources, they might qualify as a 1099 contractor, but misclassification risks IRS penalties.Wages for W-2 employees and payments to 1099 contractors are both deductible business expenses, but compliance is key.This post does not create a CPA-Client relationship.

The thought is creating passive flowing income now so I can be work optional in about 6 years or so.

Section 179 deductions may apply to assets directly supporting your business, excluding personal-use components.This post does not create a CPA-Client relationship.

With a 3-5% down FHA loan, I snagged a cozy home in a hot spot, worked from home to play handyman, and created a hedge against the "what-ifs" of life.

This will create a huge mess.

First off, I really like how you’re thinking beyond just the renovation.. you’re creating a tailored investor strategy that builds excitement around upscale features.

When they create costs they have to cover those costs.

It all depends on the work you/your clients want to do to create value and the overall game plan.

For added liability protection, consider setting up an LLC for the rental, though this may have limited impact if the mortgage is in your name.This post does not create a CPA-Client relationship.