Each one can come with its own complications.  

Investors who have tons of experience still run into massive complications with the process.

(A variation of this, assuming you can buy the note, is to have the property quit claimed to a throw-away business entity with liens attached, and then foreclose, which avoids complications with the current owner.)  

If I am able to get a HELOC from both properties, (I know you can only take anywhere from 80-90% out, so that would give me around $105,400 as a HELOC) and I have the difference of cash ($194,600 if I was basing it off of a $300K purchase price) from a private money lender, can I pay all cash on a property using three different payment types (2 HELOCs and the rest from the private lender) Or does it get complicated when you try to use more than one way?

Depreciation gets a little complicated.

What are the risks of purchasing a judicial sale apartment unit?

I have a call in with the bank - not sure if it’s too complicated?  

But, personally that’s pretty complicated (for me) and I don’t know what it gets you in your case.That’s the short of it...

I suppose it depends on how complicated is your business arrangement (not the property you are buying). 

You'll just want to be careful with things out of state, as that could get more complicated than necessary.