They may be able to help negotiate with the lender on your behalf or provide alternative solutions to mitigate the impact of the increased escrow shortage.Additionally, you could explore refinancing your mortgage with a different lender to potentially lower your monthly payments and escrow requirements.

@Slaven Slugic, get hurricane shutters for the time being in order to receive the wind mitigation credit for insurance purposes.

Without knowing your personal financial situation, I would lean towards using strategies to mitigate the $65,000 loss each year or selling SFH2. 

Consider working with contractors or renovation specialists to obtain accurate cost estimates and assess the feasibility of your renovation plans within your budget constraints.Risk Mitigation: Keep in mind that renovations come with risks, including cost overruns, project delays, and unforeseen complications.

However I also think spending a few bucks to help mitigate that risk is worth it to me.

Do I ride him out and take the guaranteed money, then mitigate after he leaves?

Make sure you factor this into your ARV (it will be considerably lower) and don't move forward unless you have a plan for mitigating the issue (or are happy selling far below market value).

We are looking for someone to help us file taxes (both for LLC and personal) for this year and try to mitigate any tax loses, but also who we can build long term relationship as we grow our portfolio.

The best reasons to carry a mortgage are risk mitigation (less equity in the property means less attractiveness for lawsuits) and opportunity costs (leaving money locked up in a house when it could be earning a better return somewhere else).

They can help navigate challenges, identify market opportunities, and offer sound advice based on their own successes and failures.Risk Mitigation: Sharing the risk with other investors can reduce your exposure and help protect your assets.