Upwelling, I believe you will want to speak with someone licensed to give you insurance advice - BTW there are some on SB, I've seen them post in the past.
I suspect you are confusing liability insurance (insurance for when you are negligent and cause injury or loss to someone) with life related insurance - which sets premium based on certain lifestyle characteristics and pays out the contract to the individual insured if they are injured or die. Life insurers ask you if you participate in certain activities... liability insurance isn't concerned about what you do to yourself - they are concerned with what you do to others - so if you are an Instructor/DM then you will want professional liability insurance to protect in case you are found negligent in your instruction in some manner that leads to a loss. As a property owner you will want insurance to protect you from claims made by tenants if you are negligent in the care of the property - but also for claims by others if your negligent maintenance of the property fails to meet expected standards and causes injury to anyone on the property... or perhaps walking on the sidewalk in front of the property... etc... These risks are related to the use of the property and how you intend to care for the property etc... not with what you happen to do in your spare time...
I would suggest you take your question up with a licensed insurance professional so they can cover all your options and specifically understand what you are looking for. Please do not construe the above as insurance advice - I can't provide that. Additionally, many of insurance particulars are very regional so you really will want to speak with someone locally.