I tried searching online for "Real Estate Transaction Case Studies", it seems like it either doesn't exist, or they have been SEO'ed to oblivion (i.e the 7th o of Google)Thanks in advance.

or put a new roof on an existing investment property?

Seems like the best move is to use that VA loan, preserve existing capital for repairs/future expenditures/worldwide plague, and then refinance into a conventional when it's time to use the VA loan again.

They have existing tenants and one of the tenants is section 8.

But umbrella goes beyond where you may have existing liability insurance and is more broad.

You will find many of the existing home are dated, but still going for top dollar due to low inventory. 

Pouya,If this is a flip, the correct coverage will likely be a Renovation Builders Risk policy to cover the existing structure as well as the renovations.   

Put some unexpected repairs into your budget and get as much information from the existing tenants and the home inspector.

My job was to bring in new business which meant existing customers seeking to refinance their mortgage loan would not count towards my target numbers.

I don't see the point of this when REITs exist.