May as well be proactive. 

Im strong believer of doing proper homework before investing in anything.. one may as well go to put money in stock that he or she don't understand.

The next week I ended up driving to eastern Washington for opening weekend of deer hunting and said “what the heck may as well drive to spokane I’m halfway there...” so I did found a few houses I liked..... anyways we made an offer on a duplex on my 30 birthday they accepted it and today the deal is done!

@James Popp, in some neighborhoods, .4 of a mile away may as well be in another State!

@Kibby Twong,All the rest aside, buying for appreciation is speculation - read: gambling - it's not investing.You may as well roll the dice on Wall Street.David J Dachtera

If the city is as small as you may think I don't think you are going to avoid competition and you may as well get all the information you need from the horse's mouth. 

He is planning on leaving at the end of May either way though because a 3br is too much for him to carry on his own.The crux of my question is do Isacrifice the earlier close for less risk/hassle in dealing with the current tenanttry to work out a deal with the tenant to allow me to take possession earlier but still allows him to stay until the end of May as he has planned?  

If the housing / rental market softens it's going to shake a ton of people out that are getting by as poor operators right now.If you aren't interested in actually being a property management company then you may, as others have mentioned, be better off getting a proven third party management company to handle it for you.Good luck either way.

At some point I may as well refinance (to keep the ROI high), or exit and put the new assets in an index fund. 

Putting that kind of money into the property you may as well put 25k down on a fully renovated property for 185k and have no problems to deal with.