Also, getting into the world of land lording brings you into a whole new world in terms of potential liability.  

You could split 50/50 with your Dad providing the money and you all of the ground work and labor or he is a private lender which would probably mean you pay him interest on the money and maybe a cut of the profits.Does your Dad want to take on some liability and be more involved or does he want to be passive.

I have a question about the liabilities associated with private lending.If i write a personal check to a flipper as an equity partner, junior lien holder or senior lien holder. does that open doors for potential lawsuits related to that flipper and the property? 

Downside is liability and I would need to do a separate self directed IRA to tap additional funds that can't be coming led with personal.2.

Wow, this isn't meant to sound like I'm simply putting an arbitrary dollar value on a life, no matter if its an eldery "hoarder" or ANYONE, but it leads right into my next question, as I've never tried to buy property insurance like you can buy auto, where the "comp and collision" is optional (i.e. they pay for YOUR car, not just the straight liability), but when you said you held off on insurance, does that mean you had NO liability as well?

If the asset manager accepts your bid and you receive the deed, my question is is there a possibility there are liens on the home or is the HUD homes with no liability for back monies owed?

Can the repairs on Property 2 offset the tax liability from Property 1?

Not even counting the liability of having all that money there in our office which would be prime for a robbery in my opinion.

Plus, why even take on the risk/liability that comes with doing such a thing? 

I just went through this exercise and determined increasing my insurance liability limits to $1 mil on both of my places was a better option.