We are also looking at setting a property up in some fashion like this in Hawaii.

Western Mass has good cash flow in and around Springfield.

The western slope?

Any local (Aurora/Western Suburbs) contractor recommendations who may be able to do it for less? 

We have considered paying ours down in snowball fashion once we have all the remodeling/repair work done that we need to finish on our properties.

Lets say the building is valued at $350,000 here in Western Massachusetts.

If you are planning to have kids next year, you are going to want to either have excellent health insurance through your job, enough money coming in to afford a marketplace policy, or become a citizen of another Western country that provides health insurance as a right of citizenship.

Quote from @Bob Stevens: @Jori Anderson we do our job :) Haha no magic, just good 'ol fashioned work!

Most maintenance things are not an emergency fix- you have time to investigate the issue, determine if it's something you can fix yourself, maybe call for an estimate, etc but if somebody's heater goes out and it's 3 a.m. in January in western PA that is an emergency fix and it's going to be expensive.

I would argue that self-management generally has costs that rival the management fee:  1)  Inability to be attentive to guest inquiries in a timely fashion, resulting in lost bookings, 2) Inability to quickly respond to repairs and maintenance during the guest's stay, "we are lost and can't find the property", and lots of other surprises, which result in refunds over the course of a year.