My goal is 2k a month cash flow.

Also  beware that  paying a large loan fee  may affect the lenders  ability to do the loan.I got cash

I want to add him to 50% ownership so we can both manage the property and access the cash flow.

With a non-spouse inherited IRA you have (up to) 4 choices:-Cash it all out now-Cash it all out over 5 years-Take required minimum distributions based on your life-Take required minimum distributions based on the life expectancy of the oldest beneficiary of the inherited IRAEach of those options has different tax implications.

I'm curious on thoughts surrounding using HELOC/ IRA/ Roth money to purchase rental property if I find the right opportunity vs delaying for a while to save up extra cash. 

Condo and cash out will 'hurt' pricing for any lender.

Coach Carson talks about the small but mighty investor and how you're way ahead of non-RE investors with a few solid appreciating properties3) If you haven't done this already put your money into high yield savings account so your cash reserves can grow 4 to 5% not a regular savings account earning 0.1% interest. 

Lending Issues on CondosWhen you're looking to purchase an ocean front condo or investment condo, I highly recommend paying cash if you can and here's why.

Cousin a does a cash out refi?

Break even on cash flow, purchase equity, appreciation?