How many times can you house hack in an expensive market (700K+)?

[Clayton Hepler]

I am looking to move to Eagle County, Colorado next year and I would like to house hack. Properties here are in the 600-1 mil price point. Has anyone house hacked consistently in an expensive market with low down payment options? I want to house hack 5-7 times over the next 5-7 years and I want to build a strategy to fit this in an expensive market. Are there any suggestions on how I would do this? I'm thinking of doing an FHA loan first. After this, what would be my options? Keep in mind that my wife will be W2 and I will be a 1099.