Why is the renter paying your down payment and agreeing to buy at a $30k premium in 3 years, plus shelling out an additional $500/month until then. 

They are generally very busy right now so can charge a premium.

This significantly increases the premiums and I'm not sure its worth it.

Be prepared to talk pros and cons. if inherited them may have stepped up basis so no tax consequence.Would you pay a premium to get terms?

Most rates are mid 5's so you're paying a premium.

Existence of the pool increases your insurance premium for this same reason.

I'm happy to pay a premium for this (no pun intended!)

If the seller wants a premium then I will want to lock up the property for a long time and get a tenant commitment and zoning approvals with site plans before closing on the dirt.

Here is some back ground.Tax Certificate, Former Owner is Still in Possession, Bought at 2018 Sale, Residential Structure on PropertyI was going to add casualty insurance to the property but was unsure if I need to wait for Tax Deed for the premiums to be included as an expense with redemption or if I add insurance with a certificate and owner is still in possession if those premiums+interest will count toward an expense at redemption.Any help would be appreciated.

However, there were multiple "coaching packages" offered for $10k ($20k for premium).