If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I like the idea of STR as it seems like it can generate significantly more income than LTR and would allow me to block out dates if I have friends or family come visit.

we do have to remember and I know its 10 years ago and many on this site are post GFC investor and know no better.. but were do you think all these deals came from... back in 2010 to 2014  it was not from well performing assets it was from stressed and failed owners. 

check to see if there is still 179 on airplanes.. and then put it in the rental fleet at a very good FBO and then use it when you want to visit your new holdings your 1031 into.. buy RV's and put them in rental fleets.most syndicated RE projects these days will have some tax benefits.. just musing here.. 

Like contractors, which can be ROUGH especially for someone with a day job who cant be on site beginning and end of shift. 

Every property up for consideration gets a visit.

And he is way over leveraged. https://www.investopedia.com/terms/o/overleveraged.asp If there is any hick up at all, the lender loses their money.

@Caleb Rehg  I would advise your first step is to search this site for college student rentals and student rentals and read all you can. 

And I have only GC ,d one project one couple mil spec home everything else I hire a GC.. who is really a site super..

Bigger Pockets is the right place to come for resources as there are plenty on the site here.