One theory is that the investors see population increasing in these areas and are willing to deal with the ridiculous local laws

Build relationships with local architects and expeditors - they're usually the first to know about upcoming zoning changes and can provide valuable insights.

It sounds like you have the basic 20/25yr 3tab shingles, which yes are prone to "flip up" or break off, esp as they get older.Find another local Roofer, that for sure taunts that they do Repairs, will warranty their work, and get the repairs done. 

Are you sticking to your local market or going out-of-state?

Zillow and local real estate agent How did you finance this deal?

Additionally, negotiating with hard money lenders for better terms or seeking out smaller, local lenders could also help.

From what I've been looking at I feel that properties that are mid tier for the market, rather than high end, can often appreciate very well as they are sought after by a large segment of the local population.

Join your local Real Estate Investors Association (REIA).

Welcome @Seth GordonI'll say this until I am blue in the face, but get involved in any local real estate groups you can.

It's good that Miguelli is working with a competent local agent who knows what they're doing, knows the local rules that apply to his situation as well as what is customary for the market, and has done this before.