Undoubtedly there will be some repairs to be made with this many tenants under one roof. 

A contractor is proposing to do the roofing and siding through my insurance, he says it will save me out of pocket money.

Let's say you can buy it for $75,000, then you figure what it will take to fix it up, amount to cover the time & costs of owning it (holding costs) and the costs to sell (real estate agent, closing costs).

But, he didn't have alot of information on the major cap ex info like roof age, HVAC, etc.

However, with alot of the HOAs covering utilities with insursnce included and the fact that at these prices we would likely pay all cash going in, at monthly costs of about $750, we should be able to justify rents over $1000 and even higher numbers with short term rentals.

At least it would cover the mortgage and some extra cash.As a side note, I couldn't make it work with an FHA because they required termite remediation (houses in LA are old) and the seller didn't want to wait (she wanted to cancel our deal).

I used an FHA loan with 3.5% down and have renters covering the full mortgage. 

Two big rules of thumb:Generally speaking, the more square the house, the cheaper to frame and roof.  

If so, are there any other charges the investor covers at closing?

Not sure who you're using but I have a mix of State farm & Foremost policies, State farm for me is about 30-40% less with very similar coverage (deductible is slightly higher & they don't cover flood damage).