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.

There's a monthly cash flow 101 game in Bloomington through MN REIA.

Of course from the rent you're paying this S-corp as a tenant.So you need to make FMV rent payments, and these payments should be large enough where you have enough cash flow - after expenses!

For newbies, I recommend starting with a turnkey cash flow rental.

(May also cut significantly into the current cash flow on it)I know you mentioned not doing a HELOC on my primary, but wouldn't it be advantageous to have the ability to pay off the line of credit instead of be stuck in a payment that is much higher? 

Quote from @Collin Hays: From a macro standpoint, cash flow is difficult when servicing debt, at least in the early years. 

This would end up getting you some tax benefits and extra cash flow that could help you leverage that into another property...maybe a 1031 exchange.

Spreading funds across 2-3 properties could provide diversification and steady cash flow.

Also I would buy tax deed land for say 2k sell it a few months later for 10k on terms that was my cash flow. 

My first goal is to hit 5k per month in pure cash flow and second goal is to hit 10k per month in pure cash flow.