If you buy the filters and call on your tenant to collect the rent and replace their filter every month, it will give you a reason to get inside the unit and at the same time prolong the life of your asset!

One prolonged vacancy can blow through your cash flow for years.

Retail can be high risk as vacancies can be prolonged.

Generally, if you have a casualty or theft loss, you decrease the basis in your property by any insurance or other reimbursement received and by any deductible loss not covered by insurance (i.e. a reportable loss).You will then increase your basis in the property by the amount you spend on repairs that "substantially prolong the life" of the property, increase its value, or adapt it to a different use.

My lawyer said, any contact with the renter could prolong the eviction.

This helps eliminate unnecessary labor costs and avoid a lot of weather delays that can prolong an ADU project.

Another question is how would the agent get her commission for a prolonged payout scenario like lease to own, or would she?

Since you're going to work in a pretty demanding profession, you may have to work some prolong hours.

These are "Tenants at Will", which in MA refers to them as month to month and only require a 30 day written notice to vacate (and you do not have to give them a reason)Of course, things can get messy if they decide to pro-long things and I need to get the courts involved, etc.Also, if want to keep them, and say force them to remove the pets, I don't want that to give me any problems.

Tenants are no fools, a good amount of bad tenants know how to play the game and know how to pro long evictions.