@Grant Shipman Great stuff, I'm a big fan of co-living/rent by room strategy, and I do it here locally in Denver metro, and it is the best strategy in today's market for any house hacker to live for free or make money while living there, but they have to sacrifice personal space.

I personally would fix the 3 windows and maybe consider cutting the rent a little more to gather more interest. 

Dave Ramsey has a good saying about how Thanksgiving Dinner is different when you owe money to the other person at the table.

I have sold some properties years ago on lease options where the tenant buyers actually exercise their right and purchased the property. ( I was in the deed.)The reason I am concerned to tie another person’s property up  with the lease option is that people can change their mind, as in the seller.  

I personally have a separate account for each property I own.

I'm still in the process of finding an alternative solution but I thought I'd leave this here as a warning for others looking to make a decision.For reference, I'll just post their email response to me here:As we review your inquiry, we would like to remind you of the following key points from our Terms of Use:In no instance shall ShinePay be liable for any of the following:"Lost revenue from service interruptions.Lost revenue stemming from delays, malfunctions of any product.unauthorized gains access to your account or due to shared passwords or if your password is hacked.Destruction to properly, places, or personal injury resulting from the installation, misinstalling, or misuse of any product.Lost revenue from entering the wrong account number for ACH or other bank transfer or money transfers or due to any delay in receiving funds.Damage to your structure, machines or car resulting from use or installation of our products.Any funds collected that are paid to a person that does not own the property.Any harm from defeating the lock and technology that controls the lock to a device.Failure to properly service any product or machine."

Well if you go together it could split it and get basically nothing - spend $2-3k file a lawsuit and get a judgment you are first in line… Also in many instances you can slap that judgment on his personal residence as well and foreclose on that.

Over the years, with personal investment alongside investments from family and friends, I’ve been able to build a small portfolio of apartment buildings with a focus on cash flow through strong operations.

I've done this with my properties because I'm well known in my small town and don't want people to know what I own.LEGAL PROTECTION: By placing your assets in an LLC, you are legally separating them from your personal assets.

It's simply factual:  you violated the lease by smoking, stop it, remove the resulting odor and that a repeat action could result in eviction and loss of security deposit.