Although you shouldn't need 20-25% down for an owner occupied residence. 

Fast forward my wife and I have new jobs about 45-60 minutes from our current residence.

Robert,Not yet, but I'll tell you what I just got off the phone with one of my close buddys that practices real estate in Florida and he is open to doing a joint venture on an apartment building in Ohio.

We require all applicants over he age of 18 that will be living in the residence to have a background check and credit check ran (through Cozy.co) The daughter with special needs is over the age of 18 but morally I do not feel right making her do a background and credit check.

Or is it a complete / private residence for the man and his 17 year old son?

The way I understand the new tax law is that HELOC interest is only deductible when used to build on to, or make repairs to one's primary or secondary residence.

When we move out of our primary residence in 53222 we will probably be able to rent it for $1300-1500/mo.

Many time when you show up in person, it not only help build relationship but they also waive the fines, after all they are doing their best for their residents by accepting non paying job and trust me it is lots of work and time they all allocate.

We have two homes in Bozeman, MT that have been rented out for 7 years as well and are currently living near Fort Carson in Colorado Springs where we will be renting out our primary residence in 5 months when we move to San Diego for a 2 yr assignment.

However, your tax hit will probably be determined by your state of residence when/if you finally sell.