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.  

Note - This determines your Federal capital gains rate.4) What are your plans with the proceeds after the sale?

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?"

Assumptions:Money Saved - $40,000/year + proceeds from new propertiesCost of homes - $100,000% down - 25%Cash flow per month - $400/home

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?

Both names are on the original deed and every other document I can find.Any advice on information I should get or how I should proceed would be greatly appreciated.

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.