Being a military member house hacking is the easiest way but I’m also open to learning new methods and if at all possible learning from others’ mistakes. 

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

Even if they do not, it’s not your legal responsibility.Long version: It actually depends on your method of payment, and it’s not always clear.Credit card payments: clearly not you problem, no 1099s needed.Zelle payments: you DO need to send 1099s for Zelle payments.PayPal, Venmo and Cash App payments: this is where it gets tricky.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

And given that, in a major city, there are hundreds of houses put on the market weekly, you need a method to efficiently screen properties to make sure they won't bleed money before you spend time analyzing, touring them ect. 

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

With that money - I am using it to invest using the BRRRR method. 

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

It will co-exist with other "new" payment methods such as google pay, apple pay and credit card etc, because the target customers are different.

Options ive looked at are the Burrrr method, house hacking with fha living in the property for a year doing small upgrades and forcing appreciation refinance then rent and repeat that every year until we reach our goal.