The biggest reason I have the umbrella is for exactly that reason. 

I think a similar approach should be taken by states with the biggest issues.

Excellent communication can make or break a relationship.Tenant Screening Process:One of the biggest headaches for landlords is problem tenants, and a good property manager should have a thorough screening process in place.

I would say the biggest factor though would be scalability.

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

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

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.

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.