I understand that I can use the principle from my Roth IRA’s but for the most part that money is locked away without paying penalties to access it.

I would like to make sure the siding is presentable before paying for an appraisal.

This past year they have started paying rent late to the point where the total accumulated time is about 3 months of back rent due.

But you'll have to either manage it yourself and develop a really good skill set in that or get a smaller company that doesn't have too many properties to manage who has a high skill set management for you, but then you need to pay for that.

If we the landlord would want to break the contract before the end of the multi-year term, we have to pay him a pro-rated fee to reimburse his investment

You are bold for taking on a non-paying tenant. 

However, just remember you do need to pay for all this.

Either the tenant or landlord can pay for the tenant screening.

If it were me, I would pay her her half of the equity and do a refinance.

Meanwhile, I created one LLC and business bank account to pay property tax, mortgage and day-to-day operating cost.