Have you tried an internship with an establish company?

Collections agencies have different levels of collection success rates and some offer credit reporting some do not.

Save and wait unless you can find a killer seller financed deal.And by relative willing to lend  you $2000 - you will want to ensure it is a gift (a true one).There is a difference between lend and gift and it can have a meaningful impact on if those funds are valid for financing sake.

Any recommendations to manage this via a different route?

If not, managing contractors and not getting exploited in the process is a whole different set of skills as well.  

Personally, I haven't encountered challenges with insurance companies yet as a real estate investor. 

I could ask 20 different questions before beginning to answer the question.

I always recommend Profit First (know how to structure your income), Never Split The Difference (good for negotiation tips) & Exactly What To Say (more sales, negotiation tips). 

I'm currently moving my investing activity to a different area and working on building my power team in that area. 

It is likely outside the warranty period, but worth a call to the company.