Here’s a bit of background on my current situation:I own one rental property that generates $1,900 per month in rental income, and it is paid off ($300K).My primary residence is also paid off ($288K).I’m currently building another rental property with cash ($200K).

I have not had any experience with Easy Street Capital, but David Lichten resides in Gardiner, Maine and I have done many deals with him. https://kennebecrealtycapital.com/It's great to have options and compare, plus he is local! 

If you own this as a rental then there is not homestead exemption and you'll pay much higher tax rate than a resident/owner occupant in SC. 

IMO this is much too little additional return to put your personal residence at risk.  

The lighting is a little dark in the picture but this will be a lovely/bright kitchen and living room for our next resident.

Investment Info:Single-family residence fix & flip investment.

I was just looking into this, and it seems that Oakland will only allow ADUs on properties with a single family residence (not multi-unit properties). 

(August 2022)Single-family residence buy & hold investment.Current Value Estimate: $410,000 Purchase price: $345,000 Cash invested: $5,000

I am a complete rookie to the real estate scene, I am looking to house hack for my first residence out of college.

My plan was to keep the condo as my residence, but after a year, refinance to fund a down payment on a multi-family property, either out of state or in the surrounding NY area.