Quote from @Steve Lehman: @William VreelandAs a local Indy Investor and RE consultant I have been flowing the IHA development closely to see what kind of developments have been happening.

It's a good place for flips; cash flow maybe not so much compared to mainland markets.

If rents are under market, consider small increases or exploring additional ways to optimize your cash flow, such as taking on another roommate.Refinancing is also worth exploring in the future.

I'm looking to add another 3K in cash flow, hoping to do it with a smaller apartment building if I find the right one. 

If you have savings, you can still utilize the VA and put more down and that will increase your cash flow in the short and long-term.

If cash flow is your main driver, not sure how well the Madison, WI market would stack up. 

Quote from @Angelo Llamas: I’m doing medium term rentals and I’m breaking even cash flow wise.

It can be done, but don't assume "they will cash flow nicely".

I’m likely staring at negative cash flow net of that high rate, or at best breakeven.

My opinion-- buy in the winter, underwrite with an extra long vacancy, get some seller concessions to defeat the cash flow if it's really that tight.