That said, even with conservative rental income estimates, my living expenses would eventually drop to several hundred dollars less than what I’m currently paying in rent once the house hack starts generating income.I do have cash reserves to weather some rough patches, but the idea of pushing my budget this hard makes me uneasy.

Therefore, it’s not guaranteed to be approved or implemented as it currently stands.

The exemption allowed results in a “taxable value” of either 75% of the “ATI fair market value” or the final Current Fair Market Value for the tax year of sale, whichever is higher.

Can you either rent out your current property if there’s been little/no appreciation, or sell it tax free?

Aim for a path that benefits the current tenants if it's worth it.

What is currently holding you back from other markets? 

There's current fire fighting and there's clean up.

I'm currently investing in the Milwaukee area.

Quote from @Aishan Gonaduwage: I am seeing good deals in Detroit that could cash flow in the current market.

With land investing/flipping becoming more democratized/accessible  (so many landed courses, tools, resources etc), current prices/RE trends etc, is it still worth getting into land investing/flipping for a brand new RE investor ?