My medium term goal is In 8-10 years create a passive cash flow of about 2500 dollars a month to supplement my retirement pension.

If so, find the best passive return possible and create some supplemental income. 

I am looking to real estate investing as a way to supplement my income and leave my 3 day a week job.

I'd be giving up about $300 in interest to make an additional $34k/year.If its relevant, I'm 29, have about 1.5x my annual income in my 401k and want to build my real estate portfolio to supplement retirement since I plan to retire well before I'm able to draw on my 401k. 

Its much like being on Supplemental Security Income or Social Security Disability, you don't trade them back dollar for dollar (though the trade is a less generous 2/1 pre-tax).

Live off of my passive income, sell some RE with my newly acquired license and supplement that with income from Brokerage funds.

It might take you some experimentation to find the right type of housing combined with the right tenant pool so that cash flow could supplement or replace income.

First if you think market rent is 1200 charge them 1200, why would you choose to supplement their rent out of your own pocket to the tune of $100/month.Second do not provide them a term lease.

Suggestion: don't take one person's view as the sole truth and stop there, instead supplement what you read by also chatting with experienced lawyers/lenders/investors and looking at the actual legislature.2- research High Cost Mortgages and High Price Mortgages.3 - sign up for news alerts from HousingWire and InsideARM.

Banking cash to live on (extra 500k) to use an extra $50k a year as an income supplement.