We have not talked numbers or financing yet but he said I can bring in an inspector to take a look around.The last piece is that I'm self employed, earning around $30k a year, no debt, around $35k in cash I'm willing to invest, though I would prefer not to spend it all on one property.  

Has anyone leased out parking spaces to self dispensing water & ice machine vendors.

He had a great relationship with his tenants and treated them like we treat our tenants for our self-managed properties.

Christian Benitez I used my self-directed 401K to purchase my first REI for 12.5K.

@Scott BakerYour self awareness is a blessing.

He is paying the loan back with post-tax dollars, so there is the hidden cost of whatever his tax rate is.The better option would be for him to rollover all or part of that old employer 401k to a self directed IRA.  

I'm currently focused on self educating, learning my surrounding markets and ultimately owning/flipping/renting properties.  

Since you did a wraparound they have a valid legal defense for nonpayment.  

I think the umbrella is a relative bargain (and as you note probably lower risk for insurer as the underlying coverage may handle many claims) for the price (I use  RLI, and maybe your solution is as simple as a lower cost provider)...In my very short time seeing inside of insurance defense, I would see the guys that worked for the major insurers (who fought claims on a daily basis) up their own policies, so that was enough for me..  

You would need to get your lien stripped in BK13 and then appeal it all the way to the Supreme Court - or wait until one of the big banks does.You can raise that defense for sure but the attorneys I've spoken to mentioned that BK judges are mostly going to keep doing what they were doing until they're forced not to.If you want an in depth article I wrote on this subject:https://www.linkedin.com/pulse/boa-vs-caulketts-potential-impact-chapter-13-lien-patrick-desjardins