Right now you have $1,000 in cash flow that can be used to fund other projects (seed money), pay you in profit to supplement your lifestyle, or fill in any gaps for underperforming properties.  

Is the option government supplied insurance where taxes supplement the insurance?  

The very tragic LA fires have generated a lot of discussion about insurance costs. People have been dropped by insurance companies in wildfire areas and had to scramble to try to find insurance - some using California...

How much will the increased cashflow supplement your anticipated SSI?

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.

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 have tons of those moisture absorber packets (from supplements, etc.) and will bring different sizes to see what works next time we swap out batteries.

- 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.

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.

You can use this property to hedge any others that you add that may only cover themselves, or require supplement until they are paid off.HOWEVER, if you have decided that your goal is to use Real Estate as a stepping stone to build wealth by upgrading the property you hold each time (condo to house, house to 4-plex, 4-plex to 8 unit, etc) then I think you are right to sell now while you think the property is at the top of it's appreciation.It will be hard for anyone on BP to tell you what to do as we don't know your goal.You are right.