I really wanted to be able to live in one to take advantage of lower entry reqts and trade rent for building equity.  

We would rather see one large claim from an unavoidable cause (tree falling for ex.) than a string of small ones.

I run adds on Craigslist and weekly trader.

You'd not quit your job to become a full-time stock trader.

MLS are working as Robinhood traders (dont want to get into my soapbox for now) Try wholesale route which is a very slippery slope and you need to 100% confident to make offers on same day .. 

Any advice/ thoughts is greatly appreciated.I have a degree in computer science and would love to trade real estate knowledge/advice for code+website help, if anyone is interested!

Many of the most common losses (fire, water damage from pipes bursting for ex.) are preventable and usually don't take a whole lot of effort to avoid.Lastly, I would just say that documenting any conversations in regards to repairs you are planning to do when a situation like this arises is always best. 

All that matters is the relationships you have with the loan traders and their perceived ability that you'll close on time.

For ex: some areas come under flood zone will require flood insurance etc.

(And there are expensive courses to teach you how to do that as a day trader in stocks with your own money, too, that are worth just as much as these real estate investment courses.)