If I am being honest, some of my biggest wins are getting through some of the more challenging projects...  

You got some great advice above from @Nathan Gesner and @Rene Hosman, so I will keep it short.My biggest piece of advice is to get involved in some of the local Chicago meetups.

This would obviously be contingent on a thorough inspection.Asking price: 1075000Annual Rent: 139kVacancy reported: 5%Insurance: 5900Maintenance: 10kTaxes: 4kUtilities: 15,600_____________________________Total Expense: 35500working on financing this week but I understand I'd be at around 6.5%My biggest concern is DOM and major repairs needed. 

The biggest thing for you to do when buying out-of-state properties is to build your CORE 4 which includes finding a great realtor, contractor, property manager, and attorney.  

You will find a TON of awesome people here on the forums representing our city who are willing to help you along your journey.My biggest suggestion would be to find some local meetups (https://www.biggerpockets.com/forums/521/topics/1211616-virt...) and introduce yourself to the host.

With rehabs you can get to significantly lower purchase prices and typically the lender will just be looking for  a100k+ ARV so that you can refinance out of the loan once rehab is completed (100k as-is value is pretty standard for DSCR loans).With rehabs experience is the biggest factor to LTV and rate so partnering up with someone for the first one or first 3 will get you significantly better terms (working in the same area can also provide benefits in terms of LTV).

The biggest challenge I see for this is risk for the equity partner because the bank would be in 1st position, seller would be in 2nd position, and equity partner would have to be in 3rd position.How do I get a guarantor aboard for the deal?

Sounds like your PM is either trying to generate additional interest revenue for themselves with your money, or they are having their own cash flow problems.

Everyone is looking for a short-sighted win of getting a monthly dividend or payout, instead of becoming deeply involved to help the company 100x the revenue in 5-8yrs while maintaining 50-60% margins.

With historical vacancy factored in, that will likely be more like $143,000 rent topline, not including seasonal A/C surcharge revenue, plus about $1,520 in laundry revenue.Expenses: Total operating expenses are running about $59,200, before depreciation or mortgage expense, and not including the offsite property manager role (me doing screening, etc).