I am in the mids of screening renters my townhouse and am seeking $300 cash on cash return, (accounting for minimal maintenance because its so new).

sounds like a good deal, 7700 potential income, you would have about 380,000 mortgage when done (1800 - 2000 / month payments) then figure in your taxes, insurance, maintenance, PM, water / sewer, garbage and any utilities you may pay. keep the current tenants in so you have some cash flow and renovate each duplex and fill them one at a time until you do them all, this will keep your expenses down while building up the income, just let the people who will look at renting the new places that the rest will look the same, so they know they wont be living next to places that need work and not taken care of.

An example is fax machines at 'copy service companies' have had maintenance wherein the whole machine was replaced. 

if you hire, figure 10% for their services, so another $420 off your cash flow, so you will cash flow $186. what about maintenance, lawn care and snow removal ?

Gross Scheduled Income: $12600Expenses (Maintenance, Management, Taxes, Insurance, Utilities (water & trash paid by owner), Landscaping, Common area electricity, CapEx, Vacancy, Internet for complex, security, etc.): $6400Debt Service (5.5%, 20yrs, 80% of cost): $3700Cashflow: $2500Annual COC: 17%I want to make sure I'm considering everything but also don't want to get stuck in analysis paralysis.

I am not surprised it is negative CoC given the cash flow is negative of course :-) I am just trying to figure out why from people talking about 10%+ target, this is not a low 4-5% but it is that much worse.. is it the area, the fact that it is new... should I be assuming much lower maintenance given it is new etc' Is low cash flow but appreciation a reasonable strategy (yet, even than I would not go with a negative cash flow of course)

I found a nice property here locally that I like and was wondering if anybody has any experience with the home maintenance insurance.

Take a close look at the reserve study and determine if the association is replacing components as needed or deferring maintenance.

Since this property mentioned they had some deferred maintenance in the listing I added $10,000 for improvements. 

After you factor in HOA dues (if any), property management, vacancy, maintenance and capex, I think you may be lucky to net $20/month in cash flow.