How do you find good affordable contractors in expensive areas?

[Jackson Sandland]

I own a large property in need of renovation in a high end ZIP code where typical building costs can exceed $300 / square foot. Crazy as it is, for this area, if you want the highest caliber work, like you would see in "Home Decor" magazine, the price can exceed $500 / square foot.

I have a property manager my family has worked with for almost 30 years who has lined up all the tenants, and would handle rent collection and managing the property. There is also low housing supply and high demand, which is great for keeping the rooms rented.

For the work I'm considering, I don't need to be in "Home Decor" magazine, I'm just looking for high quality work at a reasonable price.

I'd like to put on a new roof, update the electrical, plumbing, and decking to start. Beyond that it would be amazing to do updates including en suite bathrooms, the kitchen, the basement could be turned into another unit etc but those are ideas for when the initial renovations are completed.

My question is what are the strategies for not paying absurd prices for work that could be done with the same quality but for a fraction of the cost in more reasonable ZIP codes?

My first thought would be finding contractors who do great work in the midwest or any other area where the price is reasonable and fly them to where the property is located. The property is big enough that I can house contractors while they work so I wouldn't have to pay for hotel rooms.

What are possible issues I'm not considering here, and what are other strategies that I have not considered?

Thanks!

Jackson