Sometimes the qualitative factors are more important than the quantitative. 

For instance, higher car theft in an area/zip/city can be a factor in depressing home values.

The downside is the condo fee continues to rise every year and I’m sure there will be maintenance headaches in the future.

That's dependent on a lot of factors including what price point you are looking at, what kinds of tenants are you looking to attract, how much time do you personally have to invest in a project and so many more factors. 

They gain and keep business slowly and steadily, and are less likely to non-renew an account due to appetite issues or increases in their overall loss ratio.Insurance carriers look heavily at historical data when it comes to location, age, and weather related events (among many other factors). 

You will see a variance from lender to lender between the max and min amounts they allow you to cash out on based on seasoning and other compensating factors like exceptional credit. 12 months is conventional, not an investor-friendly cash-out product.

I am struggling weighting between handling repairs on my own (stressfully understanding the issues and arranging contractors...) as they happen vs buying a home warranty (paying premium and service call fee).

Let's ignore closing costs/broker fees etc. for now.

The first time cost me two properties and a long drawn out expensive court case which I won but ended up paying half of my settlement victory winnings in attorneys fees.

You likely do have an idea of what the most important factors are for you and some idea of what your long term goals are.