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.  

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

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.

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.

It's an estimated cash on cash return given current rental rates subtract expenses assuming 7% interest rate, 10% management fee, 5% repairs, 5% capex and other expenses like mortgage, insurance, tax. it's a estimate to tell you what properties to analyze vs ignoreyou can see the are pockets of negative returns as well as pockets of positive return. this is to supplement the data @Devin Conley provided

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

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.

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.

I also helped my mother get 2 rentals to help supplement her retirement, mistake #1b.