I saw a shed that was leaning 45 degrees with half the roof torn off for about $200k.

I also do not think you will be able to leverage to the degree you expect.

There is already a fair degree of restriction on STR properties and without paying attention to location and local laws you could be buying a headache.  

A home inspection can uncover these issues and give you a more accurate picture of the property's condition.That being said, it's possible to educate yourself to some degree to make a more informed assessment during the walkthrough.

They would be listed on the deed as the owner / co-owner with you - so there is safety there for them to that degree - plus as a cosigner they probably have great credit.  

It was just more of a theory craft for once I move out of the property for a job in my degree field.

Service levels vary by a great degree, so cheapest does not necessarily equal the best option, especially given that this is your first home purchase. 

Podio CRM is the honorary first in the Top 50 CRM for REI. 

I have an accounting degree and have been through several transactions, so no trouble following :) Makes perfect sense.

Its supposed to be 60-80 degrees this week.