Knowing how to assess a property.  

@Joshua Castillo  In terms of assessing if the property is a good investment I would also focus on: assessing the location, condition, and age of the investment property.

A lot of times when a property is bought/sold, the taxes are re-assessed. 

You West Coast rules with setting the assessment to the last sales price is a annoying...

I am trying to assess 2 things:1) Which markets would be a good fit for buying a rental property2) What criterion should I use to 'filter' which property to buy for rent and which markets to focus on: For the markets, my initial thoughts are that in addition to location and it making financial sense (positive cashflow and value appreciation, resale value etc...), it has to be something in proximity to where I am to manage it, it also needs to be more than a property to me: as in, I could see myself living there for say a vacation or in retirement (which is far away but still).

As far as there not being a plan to protect the water heater, I try to be objective and honest with myself when assessing problems so I would say that I do agree that there was not enough of a plan in place to protect the water heater because I never considered a circumstance of freezing temperatures mixed with power outages.

Make a list of all the risks and assess if it's worth it for you.

It’s not a buy and hold or a flip/BRRRR so I had no idea how to really assess it!

To possibly make such an assessment easier the hypothetical looks like the following:The residence in question is roughly $400,000 in value and a primary residence.Which would make more sense : 100% LTV offered with an APR at 8.74% (variable)  or                                                 80 - 85% LTV offered with an APR at 4.0% (variable) One of the harder things to decide is whether or not the ability to access that extra 20% in equity to potentially purchase a larger more lucrative property is offset by an interest rate that is most likely more than double at any given time.

I'm guessing there are unlikely to be any free tools for these types of comprehensive data assessments, but I'd be interested in paid programs as well if they exist.