This does also include my live revenue manager, which accounts for about $20,000 - so without her about $60k for pure software integrations.

Ideally, I would love to buy a multi-family property and rent it out, I would consider house hacking but I mainly want to my first property to be one that I can improve on and have it generate income for me.

I’m also currently looking to upgrade to a software that allows me to transfer friends from PM to owner and will help me generate form 1099at the end of the year.

You’re right, though, that you’re unlikely to generate much cash flow, if at all, if you invest in your home state.One option would be to look out of state.

I found the site after my first property, and used it to estimate my first property revenue; it was pretty close.

There are a ton of illegal basement apartments all around Hudson County--maybe 10-15 years ago there was a program (at least in Union City) where many of these apartments were made legal, I think partly as a way for the city to generate revenue, and partly as a way for the city to have some oversight, since people were renting these apartments out regardless of their legality. 

If you're ok with roommates and generating some leases, ground rules, and interviewing folks before they move in, you really can't go wrong with house hacking.

Long-term rentals offer diversification, learning experience, and lower returns but may generate lower returns.

Acquired 1-bedroom rental property, generating 30%+ cash-on-cash return.

It is very unlikely that all my properties will stop generating revenue at the same time.