.🔹 Insurance Challenges – Even when insurance pays, it rarely covers the actual cost to completely rebuild.

I live in California, this is a bay area property.were not looking to move out of state and house hacking is less palatable when a duplex costs 1.6 million.

Focus on tax-saving strategies such as cost segregation studies and bonus depreciation to accelerate deductions.By qualifying as a Real Estate Professional (spending 750+ hours annually and materially participating), you can offset your wife’s S-Corp income with real estate losses, reducing your tax liability.

If you have not heard of the Dunning Kruger effect, look it up.

I don't expect to know everything by then, but I hope to develop a basic strategy that prevents me from making the most common and costly mistakes that a newbie can make.

Here's a big "math" you overlooked for quite a few years.Right now $388k in equity, minus (let's go all out) $100k in closing costs, gets you a walk away of $288k in equity.Use that $288k as a 20% DP, and you should have $1.44M in property value,...not $415k. 

If you can rent it for $2,000/month, after fees, taxes, and potential maintenance costs, you’d still make a decent passive income.

If a prop is 250k and you can refi at 70% LTV you want to get it at 175k minus rehab costs.

The reason not to upgrade, is that you won't get that much more income for the cost of the upgrades.  

A good landlord understands that vacancies & Rent-Ready costs will destroy your cashflow and profits.