I know there's a robust real estate market there plus we're practically neighbors so it just makes sense.Any suggestions on the best ways to get the word out to investors & local contractors?

The inspection revealed rotting and termite damaged structural wood so I don't think rehabbing is feasible or practical.

While we intend to manage the property 50/50, I'm curious how practical that could be when he's living on-site.

But, if you are looking to go this route you have got to be practicing what you preach.

He is the attorney for McColly and has his own practice.

Per New York State guidelines, I will need to give a 90 day notice for rent increase, but beyond this I'm seeking any advice on best practice for broaching the topic with the tenant as a landlord.

Yes, we all get LOTS of idiots that don't read our ads and we have to politely respond to them.Best practice is to write several really good responses, politely directing them back to your ad, listing your basic requirements, etc. 

If you happen to pick up a lead or two that you can take home and practice some due diligence on, even better.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

This is just practice.