(e.g. the extra sheet of drywall, nails, tape, paint, primer, new trim boards, etc.)4.

I agree with @Eric A. for sure about making sure to keep some extra reserves on hand and factor in a monthly maintenance allocation. unless you're already doing that of course, just wasn't clear.

I'm not an expert by any means but I do manage between 500-600 apartments and I usually I don't have a lot of fight from a tenant when I deduct from their Deposit.

Those guys usually claim to have access to billions$.

It is often hard to find but they will usually have information about their tax sales. 

If anyone needs help from stuffing envelopes to showing/finding properties or cleaning houses, I'm willing to chip in where need be if anyone could use an extra hand (no pun intended).

Usually, the owner would paid the PM company and the PM company would then pay the vendor after the work was completed.

I also cannot shop around for seconds, or do any extra painting, etc..

In regards to your question a 1-3 Family in those areas will usually run you between $150-$250/month in homeowner's insurance.

The good thing about commercial ARMs is that they amortize a bit faster, usually 25 years.