I'm looking for both retirement building and daily income supplement.

With more capital at your disposal you are on a path to buy long term cash flowing assets, like rental properties or notes that will supplement your returement income, invest in hard money loans to fund others.  

You can use the cash flow to help supplement buying new investments or what not.

I’ve always worked in seasonal W2 jobs and supplemented with independent contract work, not something a bank wants to see.  

We are approaching the level of savings where we feel comfortable investing in our first property, an owner occupied multi-family property, where we can begin our real estate investing and, hopefully, grow primarily as low to mid level rental owners to the point where we can purchase a dream home in 15-20 years, as well as have a good set of rentals to supplement our retirement incomes 15-20 years beyond that (we're on the younger side, if you can't tell by the timeline). 

Another option is to supplement your income as a investor with a job that coincides.  

On my Federal tax it is filed as a schedule E form 1040 (supplemental income and loss).

I am looking for buy and hold properties to supplement my income and allow me to retire early.

That is why apartment financing terms are so favorable (long-term fixed low rates, 30 year amortization, non-recourse, I/O periods, favorable LTVs, assumable, supplemental loans).7 - In cyclical markets, you do not need high leverage to achieve outpaced returns.  

This isn't my primary job and I use real estate to supplement my other investments.