I would imagine I would have issues with the city as well.

I imagine this depends per market and what is attractive for renters or what is feasible for landlords.

I can't imagine in any market student housing would fetch 3-4X the market rate. 

I'm pretty much starting life over in a new city--well, I've been here for several months, but there have been hurdles better imagined than described--so I'm starting my real estate business anew (was licensed in NY) and starting out on the investor path.  

He deals with non-payment and tenant turnover constantly and as you can imagine, the maintenance on this OLD wooden buildings is a nightmare.

I cannot imagine spending the 30k on your existing home is going to get you a good ROI especially if you have been living in the home for 3 years. 

I imagine some investors will be wanting to downsize their portfolio to get rid of the houses they were unable to rent out.

For 39.99 I can't imagine you don't get your moneys worth ^^ (Yes, I am pre-ordered and suggesting all my friends do the same)

I would want to value the time of my Realtor and imagine as a full time investor, sending multiple requests for market data espically when seeking new markets to invest may become a bit burdensome.Any thoughts?

I can't imagine this is going to be an issue for you.