I'd be heavily focused on mitigating that future tax liabilty rather than directly supplementing that income.

You might have other options to explore to drum up liquidity (HELOC, Margin Loan, Policy Loan, etc) that can supplement your HYSA in the DP.

I'm looking to create a slight shift in my lifestyle, where I can ease up a bit on practicing and supplement my income with more passive revenue streams.

Our portfolio currently cash flows, but cash flow isn’t our top priority right now since we plan to use this portfolio to supplement our retirement in 12 years when I leave the Army.My biggest challenge is committing to an out-of-state market.

Questions/opinions on: (1) one property or several, and (2) whether to buy outright or put large downs and then supplement with mortgages.

A bit about my situation and motivation for getting into real estate investing...I have a full-time, high paying W2 job as a specialist physician that I generally enjoy but would like to  be able to supplement my income over the next 8-10 years if/when payments decline in medicine.

Our portfolio currently cash flows, but cash flow isn’t our top priority right now since we plan to use this portfolio to supplement our retirement in 12 years when I leave the Army.My biggest challenge is committing to an out-of-state market.

With that in mind, I’m considering purchasing four rental units over the next four years to build a stream of income that could help supplement my retirement by age 68.The challenge I’m facing is that the deals I’ve come across so far don’t make financial sense.

- The market is in a little bit of a lull right now (buyers market), its a great time to buy, but slower time to sell (my primary business is flipping houses) I can supplement my flipping business by providing project management services/consulting, helping investors find discounted properties, etc. etc.

How they could be more intertwined and supplement each other.