Hey @Lisa HodgesForgive me if this post sounds too simple, my intention is to answer your question.Assumptions: Assuming your goal is to attain financial freedom, meaning not obligated to work a day job, you'll need passive income to afford that lifestyle.

This 50-yr old guy wants to be job-free in 5 yrs, and I feel like there are probably tons of opportunities in nearby markets (Northern IL, Milwaukee WI, NW Indiana, SW Michigan, etc....

Greetings, CO newbie jumping into SFR investing while working a FT job. 

I have a 2nd job but I need a better 2nd job if I want to clear this thing in 2 years while not hating myself.Thanks Zach!!

Do they have a W2 job?

From what I heard from land-lords it's fairly effective at it's job and easy to use.All of this to cut my teeth on basic property management and having a close eye on the surrounding areas.

I also want the property to qualify for refinancing without having to use my personal income or tax returns to do so, as I am a 1099 employee and have only been at this job for a year so I really wont qualify.I talked to a bunch of local banks and they all basically told me that I need to come in person to meet with them. 

This year I’ve finished my degree and purchased my first investment property (duplex) while working my normal job.

I would say that urban flight would only work if there are jobs in those mid-western cities with pay enough to cover housing costs at 30-35% of income.

Don't leave you day job until you have financial freedom.