Yes, for the caulk and like @Sean Carroll mentioned, use mildew resistant paint.

There are many concerns here, and restrictions that vary by company based on the age and renovation history of a property.Valuation method: Actual Cash Value will deduct depreciation over time from your claim settle (which can be thousands of dollars), while Replacement Cost Value will not deduct depreciation, and will almost always result in a claim settlement being larger by several thousand dollars.Theft Coverage: How does your policy handle theft claims?

If the roof is aged it would most likely need to be replaced prior to the lease.

The author for LLCs mentioned that if you are the sole owner of the LLC it is possible to get personal financing rates but have the entity own the loan.

@Chris Mason Thank you so much for the mention.

@Alex Aguilar everything from 4-12 as @Bill E. mentioned.

So like mentioned above get a tax lawyer or a tax accountant and ask a few questions.

Currently I am trying to just get them to meet but they shut down the call after you mention anything about their home.

not to mention the flexibility of a HELOC vs a fully amortized loan if you can get that. 

You mentioned that it is a small raise.