How would you suggest I use this money to generate the maximum amount of monthly cashflow? 

It's not logical to lose money and now would be a perfect time to get engaged in your business.

Others will work with renters who are looking to buy their first property as an investment property.Regarding your questions, there are investors making money in this market.

Debt allows you to increase the velocity of your money. 

Money needs to be set aside for that maintenance.

Just by looking at these numbers & the fact that you have a ton of money you owe to pay down a HELOC.

The risk/reward ratio does not seem worth it, there are other less risky places to park your money with better returns at the moment.Also, as someone pointed out, you didn’t account for property management.

Maybe money is a factor...LOL, isn't it always!?

Renting rooms usually helps you have a higher occupancy but if all rooms aren't rented you net less money.

It may be a little late in your case, but since the economy is tightening, others reading this might benefit by not have their money missing when they really need it.