I would recommend getting some trustworthy eyeballs on the property to verify that the issues coming up are valid and the costs are in line.

She has stated that she will not file an insurance claim and instead expects my company to be responsible for the cost of repairs.

Mortgage liens are generally junior to government liens, therefore, additional diligence is necessary to ensure that those liens are not on title or that you are accounting for additional costs when purchasing the property.

The problem is that I live in California (which is cost prohibitive for me currently to "buy local") and must rely on remote management that is local to the investment area. 

All the while family isn't helping even when they can and the tenant isn't helping themselves because they still buy smokes/weed but hey the landlord should absorb that cost?  

Sometimes people complain about the cost of cleaning.

I'd start by having a realtor walk through it with you and determine how much things would cost to do and what it would add to the value of the home. 

We were allowed $58,000 in rehab costs.

I would not paint because it increases maintenance costs.

If this ever becomes an issue while you're in a deal everyone invested will have to pay out a share of the compliance costs to get their investment entity legal with the SEC.