Putting a property into an LLC before placing it in a trust is generally recommended because an LLC provides a stronger layer of asset protection against creditors and lawsuits compared to a trust alone, effectively isolating the property from personal liabilities while still allowing for estate planning benefits through the trust structure; essentially, the LLC acts as a shield to protect the asset within the trust from external claims.Consider getting professional advice on how to structure your assets to shield and protect the asset(s).

Any thoughts on how I might approach the conversation with them?

Well said on #4 @Michael Plaks

I cant find anything concrete on Box.com integration on their website but assuming any of these cloud document storage companies would work?

We're also wondering if FEMA sets the price based on SF, furnishings, etc.

One of the reasons why I’m bullish on real estate investing is because I am more afraid of the “what if I didn’t invest” rather than the “what if it goes wrong.”Yes, I could fail and lose everything I started with, but I’d still be farther along than if I never started at all.I’d have the knowledge, skills, and lessons that only come from taking action.Every misstep is a step forward when you’re learning and adapting.The real risk isn’t failure, it’s standing still and letting fear hold you back.Take action!!!

@Dennis Gallagheri don't really use any rules anymore, i just evaluate the actual expenses on actual properties. 

I think you really need to work with an agent based on what I am reading between the lines in your post. 

Something problematic they find that was undisclosed on your application (not saying you'd do this, just giving an example), title issues, entity issues, issues with the appraisal even if the value is acceptable...you can either bite the bullet and pay for the appraisal, don't move forward with the loan, or try and find a HML/PML willing to lend to you without an appraisal. 

If we were to split like this on our current development, our engineers would collect 25 to 35 times as much as we paid them on a straight up fixed cost contract.