@Samuel Coronado - the challenge is that there will likely be a very small number of renters looking for a house that size, as well as that can afford a rent amount that high who won't just buy otherwise. 

House hacking, if you will. 

buy house  find renter rent house maintain house pray they pay rent and dont destroy it.

I see that you recommend NOT having my mom deed the house over to me in order to borrow against it.

You are considering putting a tiny home on your existing property as an ADU or using that money to save up and buy the next investment property and wondering which would be the wiser choice.I think ADUs can help provide additional, much needed, housing.

What is she doing now in terms of paying for housing? 

Connect with other investors, agents, and property managers to get a feel for the area and learn from their experiences.Are you thinking about house hacking or just straight-up rentals for now?

I have the option to buy a 1,300-sqft 3-bed, 1.5-bath house in South End neighborhood of Stamford, CT, from a family member before it goes on the market.

I personally am interested in creating a long-term rental portfolio but I'd be interested in hearing any strategy, ie. house flipping, short term rentals etc.

I would for NOT do tree houses for liability reasons.