You may not get landlording experience but you'll get maintenance, financing, and paperwork experience.I think the discussion points in your head and with them are around what kind of improvements they would need or desire (if you have to make it elderly accessible that could be a selling point for the next tenants, but what if they want something that will cause you more upkeep in the future?)

My goal from this site is to get the education and connections/networking/friendships to help with our goal to be early retired, build/preserve our wealth, and a great happy life for my families future.

My main focus is generating the most cash flow possible to support my (future) family solely from rental income, preferably sooner rather than later.

I'm hoping to do some flips here and there and have some rental properties in the future

If you're interested in partnering up for now and for the future, leave a message or you can send me a PM. 

In the future, I hope to be able to pick your brain about driving the traffic to the site.

I think, to avoid any trouble for yourself, and to do what is ethical, is to take that savings you get back from Bob and bring everything up to code that you are aware are not up to code, and do better homework in the future. 

Given your interest in making sure each future purchase is treated FIRSTLY as an investment, whereas your previous one wasn't, it may be worth your while flipping your current primary once (or, before) you start house hacking, rather than renting it out? 

I have a property in Alaska, that I am behind on taxes on, not yet to the point of tax foreclosure, but no way to pay the taxxes in the forseeable future.

@Chris L.I would really appreciate that in the future.