I would like to build a portfolio that produces adequate cash flow at retirement to help supplement income, etc. 

My #1 goal is to one day grow a portfolio of single family homes + small multi-family homes that cash flow positively, and years from now produce enough monthly income to greatly supplement (and eventually replace) my income from my job (aka, retiring in my 30s).Thanks!

I have two beachfront condos and im looking to supplement my current insurance with better hurricane insurance and add flood insurance. 

I happen to enjoy my W-2 job, so my goal has been to supplement that with cash flowing properties that will provide additional income now and in retirement when they are (hopefully) paid off. 

I learned about supplemental taxes when you purchase.

But if you are trying to supplement your full-time income with passive income, then syndications might be a great avenue.

Best to have W2 income that is supplemented with rental income. 

I personally want passive income at a certain level over time so I can supplement my job have more wealth.

As my realtor business takes off I can hone in on investing to supplement my retirement. 

If I can't net cash flow $3k a year (a number I set for myself) prior to depreciation the deal doesn't make sense.In your case, you could house hack a 3-plex i.e. get in with a low amount say 5%, because you live there, (I don't see coverage of costs with a 2-plex if you live there, without supplementing with your own payments).I use Fannie Mae Matrix as "what I can do", https://www.fanniemae.com/content/eligibility_information/eligibility-matrix.pdfAnother example, I have also been eyeing vacation properties for my family.