Here in my neck of California the re-assessment occurs as of the date of sale so that we get supplemental tax bills in year 1 rather than in year 2.   

But I am seeking cashflow to supplement a paycheck.

My original goal of the handyman business was to supplement my REI projects

If I had a vote, I'd vote on using the stipend to supplement a house close to UH Montorse or the Heights and budget an amount to save to supplement some savings to purchase a B class property in the burbs.  

In LA County, if you made any addition to the square footage or additional unit, when you have the certificate of occupancy they will reassess it and you can expect a supplemental tax bill. 

She doesn't want anyone that close but the garage is huge behind her house I thought about looking into adding a story on and making a 1b 1b rental to help supplement her income so she is independently able to live there.

I would love to transition into real estate full-time, while also supplementing my income by doing freelance writing gigs online.

The following numbers are also provided by the Realtor attached to the selling NJ Off Market 6-Unit Rental Property starting with it's Total Monthly Rent [with Rent including supplemental heat price]: Apt 1 Rent Price for $825, Apt 2 Rent Price for $975, Apt 3 Rent Price for $975, Apt 4 Rent Price for $1,200, Apt 5 Rent Price for $825, Apt 6 Rent Price for $975.

If you are looking for a property that will "supplement" your total monthly outgoing debt to help you pay for a property that you will be living in for a few years then this may be a strategy that will work for you!

SSI (supplemental security income) is for poor disabled people without enough work credits for SSDI (social security disability income).