And please keep updates here of the train wreck of it all.

I have a free training on YT on how to do this.

Train is huge! 

I have recently been considering this same train of thought. 

As I'm sure most of you know, a long-term rental is simple since the only recurring expense I own is the mortgage, whereas with a STR I'll own the mortgage, internet, utilities, furnishings, cleaning fees, etc. which just makes my projections a bit foggier.I'm looking for feedback on the below expenses and wondering what else I should be thinking about, that I don't currently have listed.

Biggest thing IMO is getting close to the train station and have a high quality units that may not look attractive on paper the first few years but will have the ability to raise rents consistently long term. 

Look for one that includes a training video to ensure you understand how to best use it.

I would ask what their commission percentage is, how much training they provide, if they require you to be in the office, and how much their agents make on average. 

My two bedroom is currently being rented out for 1900 and the training is coming in the spring.  

If you just grab one off the Internet, it will have a lot of holes.