I understand its a personal choice for everyone but figured some people with experience can chime in!

This question is hard to understand, the grammar makes it hard to understand, and I think there are words missing. 

I understand the eagerness to get started, but slow and steady still wins the race.

Understand their fees, bid process, termination requirements, markups for work done, how they confirm fair bidding (especially if they have on-staff handyman).I would talk to the actual tenant in place to understand what their experience is with both property and management team.I would drive the area to understand how your property compares to others on the street/in the neighborhood.I would talk to other management companies and realtors to understand their understanding of the market, rent levels, etc.Basically, full due diligence and underwriting of the property.

Looking into cash-out refinancing and DSCR loans and all of that but I'm getting ahead of myself as I don't even have the 1 yet lol.Nobody in my family has any experience with this sort of thing so I'm just hoping someone can give me their opinion on if this investment makes sense.The home is currently being rented for 2900 total (all tenants are month to month and have been there about a year each) and my monthly costs would be 1,200 included taxes, insurance, mortgage etc.I am considering putting the home on section 8 because the fair market rent would make my monthly rent 4k+ but I'm weighing the pros and cons on that avenue.From what I understand the biggest costs to me as a home owner would be a new roof or fixing the pipes for any reason..

I suspect you will end up regretting selling the place in a few years but I understand your thinking.

You can’t craft an offer that solves their problems - one they’re likely to accept - until you understand the problems they’re trying to solve. 

As far as picking your lender - You will want to make sure you work with somebody who not only understands your goals but has products that match your needs.

I understand your concerns about the repairs on your 2-flat brick building in Chicago.

I understand your concern.