While raising money is an important skill, what makes or breaks the investment will be operations. 

It also takes experience in the asset class that you're raising money on.

Neither of those pencil out.I think you'd be wise to save the money and find your own leads.

If they don't, then you file a claim and hope the insurance company squeezes the money from the tenant.Get rid of this tenant.

Both of our properties have about 100k in equity in them so we were thinking about using getting a HELOC on the duplex rental property and use that money for the down payment on the next property.

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

You can purchase this with a low-money-down FHA loan. 

I could get the same or higher overall ROI by putting my money in an index fund which is 100% passive.Deal #2This seems like a good deal to me at the asking price.

You spend a lot of time and money having people do this work, and at the end of the day you don't net any more income compared to a long term rental.

Any PM software should be able to do everything you mentioned.I am not a PM but I am an Accountant/CFO for PM companies and real estate investors.