I am starting with Wholesaling because I don't have much cash on hand. 

Hello, I’m a homeowner and real estate investor in Colorado Springs with over $300,000 in equity in my current primary residence and an additional $50,000 in cash reserves.

If not I would not do a HELOC or cash out refi on your primary, I would just continue to save.

Because it is a college town, I’ve been renting by the room in order to cash-flow, but this has been somewhat of a hassle.

.- Risk to Watch: Overconfidence in Cash FlowCash-flowing markets can shift.

Since inception, the property was negatively cash flowing due to the increase in interest rates.

If you're seeking initial cash flow, declining cities with cheap properties may provide higher initial cash flow, but they won't provide lifelong financial independence.The rental income requirements for lifelong financial independence are:Rents must increase faster than inflation.

If your goal is to rehab the property to increase the ARV, it may be more beneficial to close on it with cash or hard money and then do a Cash Out refi with a DSCR once the property is turnkey ready.  

For my next investment, however, I'm seeking cash flow.

Make sure the numbers work: confirm cash flow, verify rent comps, and review management fees carefully.