This is just the latest in an arduous process, to find the deal under market value on the land, rezone it to multifamily district (long and costly process), permit a six suite rental (difficult with many technical fire code and structural engineering challenges), build the units (using all my experience in home building and every possible favour and technique learned over the years to project manage), get financing to finish construction (from a private lender after the bank lenders totally dried up on this type of financing), and pre lease the units while under construction to quality tenants.  

Even if the roof repair is covered by insurance, is it best to avoid it for smaller things to avoid increased insurance premiums?

That's worth having a high-quality tenant and it should be worth it to them to avoid moving, paying more, or potentially winding up with a nasty Landlord.If there's even a chance they would cry over an increase, be prepared to show them comparables, the value of staying with you, and how much you are losing by keeping them at the lower rate.

Read a book on repairing homes.

@Matthew Pease most credibile and big flippers have their stuff and quality together (whether they are permitted or not I would argue that few go through and get the proper permits). 

Also, a conventional loan will not pay for the repair costs, so that would come out of your pocket whereas a private or hard money loan may cover most of it. , the method is meant to make for a quick turnaround. 

I believe in quality verses quantity so I would take less ROI if the property is of better quality.

We currently own one single family dwelling renting for 1.79% of the purchase price and another that was going to be used as a rental but after digging into some unforeseen repairs, we are looking at flipping and using the money to either purchase a new rental or pay off the first home outright and be free and clear. 

Does this cover your payment with taxes . insurance, and a little for repairs? 

The downside is that the nature of project competition means you can get lower quality work and find a disconnect with those you work with since they are looking for more short-term work.