Once you get it rolling these entities make life much easier, it can just be a pain to learn how to run things differently.

On the other hand, it was a pain to constantly have to be on them about the rent. 

Only then should you build systems around the things that are painful for you.

It is painful at first but I promise you it will pay off!"

Even though they've got the best tap on the market, first access to on-market inventory it's just tough to do there right now due to the high entry point and exactly the pain point you're facing.. the inability to cash flow with only 20% down. 

I know smaller Landlords that use Venmo but what a pain!

One advantage is the the university provides a steady economic base that usually doesn't waiver too much during recessions.People think about colleges as just students and professors, but of course there is a whole army of people that work in maintenance, administration, etc., just like any large company.

I feel your pain on capital raising, 60-120k on even the most basic properties in decent areas is a huge barrier to getting started.

If I get a 3 night orphaned slot I'll lower my minimum night stay ( a pain on Airbnb, easy on Vrbo) since I can get $300 to $400 per night in the summer. 

When it comes to these government agencies no one has the slightest clue and its a painful process to uncover the drama.