Your responses provide me a lot of comfort and it seems like everyone agrees on the next step(s), which puts me at ease.

Do your due diligence and work with your real estate agent to get comps. as long as the numbers make sense and you are getting a cash flow that you are comfortable with, it should be a good investment. 

Assuming a reasonable insurance payment for a family of 4 (say less than $1k, which is what passes as reasonable in the US), are you comfortable living on $10k annual?

Initially, you may want to make this “$0” until you are comfortable with your PM, and also layout the preferred method of communication – I suggest written so there is a paper trail.

It definitely takes a little longer to try and get comfortable with the feel of a market in my experience than simply knowing your city you live in. 

It is a matter of whether you want and/or feel comfortable with management.There is truth to the theory that self-managing will educate you. 

And these are the groups that I feel comfortable recommending.

I would advise not to get totally comfortable with the "one-stop-shop" feeling at that point and be open to shopping around for better terms or rates with other lenders if you can get them.

Costs will be higher with this route, but it would accomplish your design to not have any one individual "on the hook" for non-performance of the loan.However, I'd encourage you to either be comfortable with the liability in the deal or to not do the deal.  

Furthermore would the comfort level justify gas.