If she is owner financing, tells me its paid for, and has told that it is currently rented and has rented well in past, why would she rid of the property.Why would she force the price so much higher that the tax value(market and assessed are similar to tax value)?

Tax assessment alone is over 50k.

To properly assess the whole picture is needed.

Ask for these things: - their current budget, - how the actual expenses compared to last year's budget, - history of special assessments and when they expect to issue another one.

Begin with the MLS Home Page instead of search functions to look at properties and that may lead you to general trends.Well, I'm not agreeing with that analysis or assessment of rehabbed vs. leased or other sales.

Hopefully someone on here has similar experiences with this.So my question is if they do not renew, how would I go about assessing damage and then putting them at fault and using their security deposit?

I have a comprehensive lease that I use.

They do tax assessments for many towns in MA.

I totally agree with your assessment of the Orange County REIA club and that is why I switched to a new one that started two months ago. 

Though I can respectfully disagree with others assessments on how they grade a property, there is no true set of criteria for doing so and this is why an investor should really do their own homework on areas and markets before they buy.