Use tools like the VA loan for house hacking and your Basic Allowance for Housing (BAH) to cover living costs while building equity.

Once the above skills and tools are acquired, understanding the sequential process of the development along its timelines and costs needs to be correctly implemented.

Don't depend on Aircover.Homeowners policy will not protect you if your renting as a STR.You need the correct STR policy to protect your property.

You defiantly want legal protection as stated by @Max Wilhite@Jonathan Bock is correct about keeping it simple. 

Is my thinking correct that homes in highly appreciated areas won't benefit as much from Cost Seg. 

Quote from @Zara Massoud: Your new PM is correct and the old ones were wrong.The property manager must have your social security or tax ID number on file.

I ended up having to pay for their tax preparer’s time to meet with me and make corrections.

They lower taxable income for federal taxes but not for FICA.However, employer contributions made by the S-Corp are not subject to FICA and count as a business expense.Make sure your W-2 correctly reports wages, deferrals, and FICA wages.

Are there specific steps or systems you follow to ensure it’s done correctly?

In my view they made the correct decision and if you spent significant time recovering this cost, well I think we all know what that is.