You just have to be driven and consistent and know how to cold call. 

I am 26 now and If I could start over again the #1 thing I would do is go to more meetups, CONSISTENTLY.

There is usually a higher business cost to use those experienced contractors who are properly insured and have a great track record.One of the few times I see investors get a great rate and high quality work is if either they employ the contractor directly so their jobs are the sole focus or they do lots of volume to give a contractor team consistent work.It sounds like you are playing in the one off space with an non-certified contractor hours away from where you are.

There is obviously some value to having the cash in a lump sum, but there is also a benefit to consistent interest income, so it feels like a steep discount of 20 percent or more is unwarranted. 

In particular i'm wondering if the areas around Hopkins (or their medical school) are good for targeting students, or if there are other neighborhoods that can be easily and consistently rented.

Whatever you do decide to do, BE CONSISTENT.

Most loans loosely track the 10-year T-bill and the rate on that has been consistently dropping despite a relatively robust equity market, there’s even talk of rates going negative without the Fed actually pricing them below zero itself.So, in terms of interest rates at least.... probably safe after 5 years.

All this means, having good, eye catching photos helps a lot, but it is not the first thing people will notice like on Airbnb.Lastly, and I know you didn't ask this, STRs are a lot of consistent work.  

The Rock County market is extremely beneficial to investors as it allows you to consistently see 1.5-2% rent to price ratio.

(remember who coined it @Brandon Turner  :] )Here are some OCD study habits that I've consistently carried out along my voyage:-taking detailed notes that appeal to me-writing down my favorite episodes, as well as a bunch of other useful data/information points.