This really puts things in perspective and helps me what I would need to do if I consider utilizing this strategy.

What is the best way that you have found to tell them that you need labor & materials separate, so at tax time you can send them a 1099 for labor?

Maybe an investor is flipping a lot of properties and you could offer to pick up and deliver materials to his crews, clean the work sites every night, bring his crew lunch, or whatever.Find a way to make yourself useful to them, and they will reciprocate.

My original plan was to utilize a real estate agent to be my property manager that I met through a Dave Ramsey referral program, but I'm exploring if I should attempt this on my own.  

I'll be moving from California and only making a 50k  salary, but this job will cover housing and utilities.

A good baseline is to calculate material costs (e.g., $300 for paint and supplies) and add a fair hourly rate for labor.

While the cost can vary depending on the scope, zoning, and materials, I’ve seen similar projects run anywhere from $50,000 to $150,000, depending on factors like plumbing, electrical upgrades, and structural work.If you’d like, I can connect you with a few contractors or architects in Chicago who specialize in basement conversions.

My preferred options are:1. house-hack with a duplex under ARV; live in one unit => renovate => rent the other unit2. buy a SFH under ARV that could be converted into a duplex (preferably adjacent units vs top/bottom) - I'm assuming the biggest challenge with this strategy would be separating the infrastructure for utilities; and costly.

Quote from @V.G Jason: BP agents are gutter material.

I individually priced all my materials and got several estimates from contractors.