I also keep the total amount of all my insurance deductibles for each property in reserves in case emergency comes up.

(Utilities at the street)Obstacles: I had the first title company pull records (600 pages) who said their underwriter won't approve the deal for title insurance because of her appeal and court history.

4: How reluctant were they to find a good solution in case you ran into an issue ( foreclosure, delay in payment, insurance issue )with borrower after buying the property?

But I've been trying to justify house hacking, and without using an FHA loan (I'd rather not pay the extra insurance) I'm finding it hard to see the benefits.

Call your own insurance agent to get a quote for the building.5. 

Do I have to prepare extra money in my self directed Roth IRA for maintenance/repair/tax/insurance if I invest SDIRA into  LLC ?

Make sure you get the property taxes and insurance costs down.

Here are the numbers:Monthly Payment: $1,255.60Principle balance: $177,466.11Principle: $301.61Interest Payment: $555.52Escrow Payment: $398.47Mortgage Insurance Payment: $125.36Additional Principle I pay each month: (Roughly) $144.40, to make the monthly payment an even $1400.I was given a rough appraisal of about $275K to $290k, and I know id need to meet the 75% LTV rule, so there's probably not as much Cash out equity available as I'm hoping for, but I figure Id see what my options are.  

Owner also has property tax, insurance, and outdoor upkeep.$78k annual rent with ability to add $1500 a month for vacant space.

I got  more time from them, butI  still have to change insurance companies.