You should always opt for the title insurance, regardless. 

Also, the contractor will(should) have insurance and if the amount is not great, will probably pay it off before taking it to court too, if you have docs from the utility company stating that they were all billed for the one unit.  

In looking for an eviction attorney I would look for someone who has experience in eviction court and knows how the judges in your area deal with both standard and funky cases.

Your offer will have to go through the agent, and you will have to use the standard local contract forms.  

Worst case scenario I can imagine without having it would be something like your tenant burns the house down, maybe somebody dies in the fire, maybe not..but in any event, you file an insurance claim and the first question the adjuster asks you is "did you have a CO?"

I average $500/unit in cash flow (each 4 unit building gives me between $2000-3000/month in cash flow after paying mortgage, taxes, insurance, maintenance, utilities, cap-ex reserve).

What about cost of insurance?

Yes, its pretty standard.

If there are too many renters vs owners traditional financing becomes nearly impossible or if HOA doesn't have enough money in reserves or enough liability insurance then its most likely that financing won't be possible.

Owner will pay all taxes and insurance on property until you purchase property at end of the term8.