(WI taxes on my corporate income, concerns from my employers perspective, etc.)Scenario 1: Request my employer mark my work location as 'Remote'. 

Have you considered a furnished corporate (mid-term) rental for increased cash flow?

Let's dive into the exciting world of waterfront condo investments and explore their potential for generating lucrative vacation rental income.

Yes, you can absolutely purchase a property with a conventional loan and honor the existing tenant lease.In fact, many lenders view occupied properties favorably because it means there's a guaranteed rental income stream from day one.

I heard about your estimating cost book from Brandon Turners Rental income book.

That will allow you to buy another home as a primary and reap the benefits of the increased passive income & deductions.

Here's a simplified and effective approach: Gather Information: Obtain details about the property, including its purchase price, estimated rental income, expenses (such as property taxes, insurance, maintenance costs, and property management fees), vacancy rate, and any financing terms (e.g., interest rate, down payment, loan term).Calculate Gross Rental Income: Determine the total potential rental income the property could generate annually.

@Whitney Lares I kept my first BRRRRs as LTRs, I know MTR and STR have higher income potential but my goal is time and income, LTRs provide me that and the management of these in STL are much lower monthly % so it works for me.

This is a much better deal then on income, especially if you area self employed. 

So self insured or not, and corporate veil piercing or not, only 500k is coming from insurance.