On the surface, it appears to be a straightforward role, but it becomes far more challenging when faced with issues like non-paying tenants requiring eviction or broken systems that haven't been properly followed.As a self-managing property owner, it is absolutely doable—but success depends on treating it like a business.

The thinking on this is that although the buyer utilizes what appears to be a purchase contract, it is actually being used as a purchase OPTION, and as such an option contract which clarifies that the purchaser is actually obtaining an option to buy should be used.   

I think the general idea is that areas like finished basements, or cape cods with sloped ceilings on the 2nd floor have finished space that is not equivalent in value and use as other finished spaces.

Accept whoever applies" is an idea that would cost you a bucket of money in the long run.Bankruptcy is usually a "no" unless it appears to be a one-time event caused by something out of their control such as a massive medical bill or a business failure. 

As for your other questions:It is currently on the market and has been so for several monthsI don't have anyone representing me yet...trying to learn as much as I can before taking that next step with a realtorI don't know why the owner is sellingI don't know the standing of the tenantsRent appears to be at marketAssuming 10% vacancy rate, my calculations show that it would indeed cashflow.  

But I believe that if you're not violating any terms, not in a restricted industry or involved with anything deemed risky by Stripe then you're probably safe.It appears their move to Stripe is for accelerated payment processing, which is interesting since they acquired eRentPayment and Payment Report.On surface level it might be they're adding Stripe as an option on top of their existing infrastructure.

Most if not all of my income appears on my Schedule E as rental income from a college rental portfolio that I self manage.

It doesn't appear so to the layman. 

If its a New Western deal though I am extremely dubious .. those require extra due diligence as the deals I see coming from them one needs to verify every aspect of what your being told.Due to the response of a poster above, it appears I was not very clear in what I was trying to say.I was trying to say that most of the people cheerleading like finding off market deals is easy Haven’t done it themselves. 

Good day, Derek,Based on what you have presented this investment appears promising, offering a strong cash-on-cash return and ample opportunities for value creation.