I always carried high deductibles and insurance was more about catastrophic events.   

This is especially true of small mom & pop businesses in high end areas.  

Also, providing value to others at a high level will pay off for you in the end if you stick with it.

If one has high living expenses, cash flow doesn't mean much and I definitely understand going for appreciation first.

However, while I was still getting contractor bids for different projects, I found 3 different companies that are quick (based off of their contracts and guarantees) and have good quality of work (based off of previous and current investor feedback) but come at the cost of price.

I highly recommend them! 

You can buy a set of five for under $300, subscription for the recording software is $10 a month, then the cost of WiFi or hotspot.If you've already had a couple break-ins, you are obviously in a high-crime area.

If you can come in and operate effectively I think you'll find success rather quickly due to that.BTW - for a property management platform I would highly recommend Buildium.

I assume it’s not high enough that you or any family members want to take on the job?

My recommendation would be different if you were a high-income earner or if you wanted steady equity growth.