. $400 a month for utilities, $500 for misc expenses like toiletries, maintenance/repairs, landscaping etc. $150 a month for insurance (this might be low?).

Detroit would be a difficult market to utilize a DSCR loan in due to the low amount of monthly rental income coming in. 

I will be sure to utilize the bigger pocket resorces.

So, I don't just factor in hard expenses like mortgages, taxes, insurance, utilities.

Hey Dee, BiggerPockets support is super friendly and quick on their feet. https://www.biggerpockets.com/contact-us#customer-supportScroll down to the bottom of the page there's a contact form you can fill out and they typically respond in a few hours. 

Give them a triple net lease (meaning they pay rent, and they're also responsible for insurance, utilities, and maintenance).

Built in 1890, this Old Victorian was converted into a duplex in the 70's by a talented architect who made some unique and extraordinary custom design choices (read Vaulted Sunlights) that make this property truly one of a kind.

Should I get into contracting with a flipper or custoM home builder for 50k a year 1099 and start my own llc and be a “real estate professional” and learn the ins and outs while making less money at first,  or take a sales job 9-5 that makes 150k a year w2 and build up capital first. 

You need to investigate and figure it out.If you include utilities with rent, I recommend placing a limit so the tenant is responsible for excess use.

If you are planning to use a DSCR loan, lenders will want to see a valid lease, utility bill, or official document supporting you are living somewhere else.