I use the Zelle app to collect upfront money from tenants and it is instantaneous with no take backs but it is not automatic so I doubt you could set it and forget it.

if you are looking to get out of the 2nd job and get some time back being a hard money lender or other "money man" part of a deal is about the most passive you can be.  

Or if things are that slow in the off season , shut it down , if the rent is canceled out by the cleaning , you are still losing money , electric and wear and tear . 

@Chuck DreisonI have seen them 90 days to 3 yearsWhere I see them more in on hard money loans as some already have interest prepaidThe 3 years were on 2nd position notes which were newly originated and down payment assistance

Owning a property with the sister is about impossible as she is not good with money or business minded.

It gives you valuable experience as a landlord firsthand which will be helpful down the road when you consider a BRRRR strategy with hard money.

You can offer them cash for keys-give them money to move.

He is a mentor of mine as well, and is not so interested in making money but rather he told me that he likes to see 7% in his passively invested accounts, so I offered and he accepted that I would pay him 8% APY On the principal that I borrowed. 

Given your question however, I get the sense that this might be your first time managing a project like this and so would strongly advise that you connect with a General Contractor that you can trust as it will end up saving you a lot of time and money over doing it on your.

They believe putting it on the MLS will make the most sense to them.Like everyone else, we are always willing to partner with people that want to learn through experience and find more propductive ways to find deals.There is money to be made in real estate in this current economy, if you find deals that have not yet hit the MLS.