Seller get $282k, buyer pay $300k.Option 2: Contact price $282k, the term change to buyer cover agent fee.

I believe I can ask for higher rent and deposit, but wondering if the risks are worth the added income.I'm reaching out to my insurance carrier to understand if my coverage needs to change. 

I’m planning on putting my rental properties in a trust and using umbrella coverage for liability protection.

One of these are requiring me to replace the roofs on 2 outbuildings on the property I am purchasing within 30 days of binding coverage and want a signed contract with a roofing company prior to coverage.

You will need to supplement your tennat $2500 rent out of pocket to cover the expenses on this property. 

After a few years, you can refinance to pull out cash or get a supplemental loan (if available).

My insurance broker, Sobie Insurance, has several companies that provide insurance coverage for Airbnb rentals. 

., for my properties I have been using Foremost insurance with normal homeowners coverage as well as general liability umbrella. 

This is important because if you want to look in several states but are working with someone that isn't licensed in every state you would want to plan ahead of time to have several agents that could give you the coverage needed.

In my opinion since you have an equitable interest in the property you should be able to get basic coverage in case of a catastrophic event.