We personally prefer to collect our rents every month from our tenants vs. some sort of electronic payment system because it gives us the opportunity to humanize the way we deal with our tenants and it gives us the opportunity to be more friendly and allow our tenants to tell us about their personal and maintenance issues e.g. tenants will tell forewarn us about health issues e.g. we've had several tenants who had liver problems and they expected to pass away within a few months.

Once people see we can live rent free, financially independent lifestyles through intelligent investing, folks begin to become curious. 

As a house-hack, you might be able to live rent free with a fourplex, but that may not be easy.

Eventually I want to get a duplex in NYC to live/ rent out.

Bay area transplant, flipped few homes in bay area, recently moved to AZ and wanting to meet people and network. 

In my early landlording days  my very first tenant was a 'professional' and her goal was to live rent free for as long as possible , and in the meantime, make me jump through many many hoops.

We will people with foreclosures that went a short period of time (6 - 9 months) if they have a clean credit report for the past 2 years.We will never take tenants with any evictions or if they ever forced a prolonged foreclosure as 1) They have tasted what it is like to live rent/mortgage free and they just might like the taste of that  2) They probably know all of the loopholes and stall tactics in the book as well as every obscure right they have.Pass on them.

The judge may grant an extended time before they need to leave, but how can he legally mandate you to allow someone to live rent free.

You just don't want to be taking money out of your pocket so your tenant can liver there. 

I think a MFH is my best bet to live rent free while obtaining my first piece of property, but maybe it isn't the smartest option in an area with such an expensive housing market.