The fact that he doesn't even want to move into a renovated unit is in your favor as it sounds as though your reno efforts may be a waste of time and money in his case.

The property obviously cash flows, so I'm torn between just ignoring it and keep collecting the rent... speaking up and giving them a pep talk (which is a waste of my time)... or putting it up on the market and letting some other heartless bastard worry about it.

I know it can happen but I have watched so many deals like this die it makes me skittish to ever try another one (so much time and resources wasted by myself and my friends in the past).

Does that have any effect?  

Thanks, @Frankie WoodsWhen newbies send out letters and they do not know what to say, when to say,  and how to say it to home sellers, they are wasting money and time.Dont be a One Trick Pony, Be a Transaction Engineer. :)

Thanks for your time,Joey HarperDriving for dollars is probably the most effective and lowest cost of the options above.

I too am new and wanting to get started with little money so I don't waste my time on filling my head full of stuff I'm not ready for right now.  

So, without wasting your time get enrolled yourself in Indus Edutrain which will show you the way of your success.

If I'm assuming correctly the attorney has a very important role here so wouldn't they be the the most cost effective point to at least start off with?

If not, it'd be best to share which city this is in so locals can chime in.If this is in SD, there are a number of active multi-family buy-and-hold folks (myself included) active on BP who I'm sure would be willing to help make it happen for you.And, to your question, your next step is to figure out how likely it is you can get it under contract - in the current market, it's common to waste time thinking about things that are off the market in no time or won't actually get under contract for whatever reason.