Let me know if this case study is helpful. 

I want to learn from this, can someone provide some feedback here and advise on some other avenues I could have taken (when private money isn’t necessarily an option).

The information contained in this post is not to be relied upon.

Most lenders will not offer this type of help or even suggest these things and simply run a generic "Pre-approval" and email you a letter.Instead with VA 100% loans it is wise to have the bank/lender runs an "ELA" Express Loan approval which is an actual underwritten guarantee to close in (15 days) or less.

Does this confirm the fence is on theirside?

"Has anyone done this with Bob Diamond."

I just got my first deal under contract any tips on what to ask or how the conversation should go with the title company is appreciated

Do you have any friends/relatives who would either borrow you the money or partner with you?

So, they’re a real good alternative to consider; however, in this era of low cap rates these loans may not result in any cash flow (expenses always seem to be higher - the a/c unit needs to be replaced; the small roof leak reveals that the last roofer neglected to install underlay; etc - tenant do more damage than the security deposit and replacement tenants with decent credit take longer to find).  

You will be well served to enter into this strategy with as much knowledge possible on how to maximize rent with section 8, how to vet tenants, especially if you're going to be sharing a building with them, and to do a reality check of whether your strategy will really work.