You may not get the first property you offer on because if it looks good to you, you will probably have competition so start offering on properties that fit into your personal investment philosophy and meet your minimum financial requirements. 

We have an LLC that holds real estate but have run into issues refinancing through the LLC when family is renting or ultimately living in the property so I’m also not sure if this should go through the LLC or be a personal purchase?

They are basically the same as applicant number one except there is an opportunity for them to make more money with the second person if they chose to work which means higher probability you will get paid on time. 

You should get these things for all applicants:1. rental application with employment reference and personal reference2. credit3. past landlord reference4. check for eviction historyMost apps like RentSpree include all this in what the tenant pays to send you a report.I cosigned for my daughter and her boyfriend on their first lease.

Hire a company/person that is solely a QI like @Dave Foster they do it every day and will keep you legal and on track. 

On the other hand, this phrase is often used by the likes of Uncle G (who, having an accounting degree, should really know better) to suggest claiming personal expenses as business deductions.

And also you sit down with your lender in person etc..

Given the details you provided, I personally might not want to settle this in mediation with this tenant however as I'd probably just want a judge to cut through the BS and tell them to pay up and get out at this point.

@Bryce Cutler I will look into it and would love to connect in person if you are attending! 

For example when someone wants to have financial freedom and spend more time with family, but then sets a goal by creating a heavy active income stream that involves their personal involvement daily.