The biggest thing I would tell you is that as long as you build a strong CORE 4 you can invest anywhere.

Hello all,I have been contemplating getting a vacation rental but biggest issue would be financing.

That contains the downside risk.So where does the remaining 25% to 40% (plus closing costs, renovation costs, etc) come from?  

I would say the biggest factor though would be scalability.

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.  

My biggest issue was the lack of communication which we discussed.

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.

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?

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).