Is it foolish to consider using the HELOC for the down payment?

It's fantastic that you already have reliable connections to assist you with your flips.

If they are, I would pay them off first.I would invest in a different market(likely bigger market) where you can find reliable contractors or find a PM that will be able to manage the properties.

Which do you think a tenant will pay first - their car or rent payment?

Focus on areas with strong rental demand, like Broad Ripple, Fountain Square, or near universities like Butler and IUPUI.Maintenance Costs: Indiana weather can be tough on properties, so budget for seasonal maintenance like snow removal and HVAC servicing.Additional AdviceKeep an Emergency Fund: Unexpected repairs or vacancies can arise, so having 3-6 months of expenses saved will help you weather any surprises.Build a Reliable Team: I have lists of contractors, handymen, cleaners and property managers if you'd like me to send.Good luck with your property and future expansion!

Your payments are known. 

I would say keeping their crews busy is a must when there is always another investor who needs a good reliable contractor.

So, I am indeed getting monthly payment from my buyer that would cover both monthly mortgage payments and also provides me interest only payments on the difference between the sale price and mortgage payment. 

If your entity has several years of operating history and good and reliable financials, you may be able to find something. 

Yet the payment processor is issuing the 1099-K to the property management company.