Anyone in the same boat (great day job but looking for that supplemental income/investing potential) have any tips on how, what, when to start and get the ball rolling?

Or, they just want to supplement their income with real estate.Many investors can get 30+% IRRs in their real estate portfolios but that does not hold a candle to the 100% return from their 401k matches. 

The duplex you own - you said it does not cash flow, but supplements your expenses?

Transitioning into our real estate biz, along with supplementation from investment properties would be ideal by the timeframe given would be ideal, but might be too aggressive.

I'm sure you appreciate that he's taking good care of the house and doing small improvements, but as you said your costs are going up and you shouldn't be expected to supplement his living there.  

You can wait to refi and save some cash-flow to supplement the refi money for the next deal if you need to.

To those in the BP community who took the leap what have you been doing since leaving your w2 job to help supplement your lifestyle on top of your investments/flips?

I would never voluntarily supplement any tenants rent given the legal ability to charge full market rent immediatly.

If your supplementing the guys income by free rent a free meal is the least you could do .

I also intern at various firms throughout each year to help supplement my costs of living.