I feel there is a great opportunity for us here with these leads and just want to make sure I am completely clear on how to position the negotiations. 

You can still show a paper loss position.

That’s a huge chunk going to IRS which stinks, but I’d take the trade off of being in a position where I had to pay such huge taxes!

My only condition is it would be a part time position to start due to the time frame I am looking to purchase my first property and would be holding my full time position until that point.

The property should be able to have rents that easily cover the payments as well as cash flow positive (money into your pocket every month). 

That's my way of positively suggesting that you don't need a $10k-25k "helping hand" invoice...

Professional landlord" is not a tax term, so I am not positive about what your CPA meant by that.

Also as the tenants pay down your mortgage you can use that equity for other real estate transactions.While hiring a PM is very daunting and we tend to get a bad reputation it is possible to have a positive experience with a PM. 

We live in CA, so cash positive opportunities are generally far from home.  

@Brent Coombs, I'm sure what he is looking to do is replace the current mortgage with a HELOC, and then some. i.e. replace his 100k mortgage with a 200k HELOC in first position and pay off the current mortgage.