@Cory MeliousGiven the clear lease addendum and initialed acknowledgment of the rules, you’re in a strong position to recoup at least part of the repair costs from these tenants.

Even in landlord-unfriendly cities like NYC and San Francisco, major investors are drawn by strong demand, high population density, and historically stable property appreciation.

It sounds like you're in an ideal position to transition into real estate investing, with both your industry experience and a strong local market at your advantage.

. - Are you okay pushing more and having to re-lease the unit, or would you strongly prefer not to have to do that and give up more on cash flow- What do you personally feel comfortable increasing the rent for? 

Build a strong network of lenders, partners, and contractors to achieve your goal.

It sounds like you’re at an exciting juncture with your investing journey, and your professional background in commercial real estate is a strong foundation to build from.Your goal of creating a portfolio for financial flexibility and a legacy for your kids is inspiring, and your hands-on approach with modeling and management is a huge asset.

With today's market I think it's important to get creative with sourcing/structuring deals in order to make them strong investments.

To protect your margins, it’s crucial to have a solid understanding of costs upfront, consider negotiating long-term prices with suppliers, and prepare for possible delays in renovation schedules.In both scenarios, it’s often safer to focus on markets with strong fundamentals (stable job market, population growth) and properties at or below the median home price in the area to appeal to a broad buyer base.

As for your scenario of exchanging two Airbnbs into an apartment complex, it could be a good move if the complex is a strong investment.

You'll need a strong stomach.