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.

How much will the increased cashflow supplement your anticipated SSI?

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

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.

Loan Programs: Conventional loans (>$7.5M), small balance loans (<$7.5M), lease up / near-stabilization loans, 2ndlien supplemental loans, student housing, seniors housing, MHC, green financing, etc.2.

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

If It is a wholesale DSCR lender that also does TRID loans, they might require a bit more paperwork, such as a VOM, mortgage statements for properties currently owned, and credit supplements on mortgages on your credit report.

Has she even received a supplemental tax bill yet? 

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.

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.