Your end plan needs to be to get rid of this tenant permanently asap before she causes a infestation in the entire building. 

Permanent urine stains.

It's been driving me nuts that for every little job that I'm too lazy or incompetent to do I have to pay someone else hundreds of dollars just to show up and take care of it, but I don't really have enough work to hire a permanent worker (16 units in Austin).

Best thing is that these funds roll into permanent financing and you don’t have to wait years to save enough money or get motivated to actually redo that kitchen.

If you are planning on holding more than a couple years, I would have a plan for permanent financing on these properties.Finally a question, when you boss says go Multi Family, are you sure he means a triplex?   

I feel like I could be pretty resilient from investing in the stock market for a few years but I guess I will never know if a bad deal would permanently scare me off or not since I've never owned a home before.Do you think rather than finding an amazing deal it would suffice for now simply to find something that could reduce what I would be spending on rent somewhere and then continue to search for good deals?

On the off chance you decide to hold and rent, make sure you discuss permanent financing options with a couple of banks/mortgage brokers up front as well.

From here he's going to come back to fix more permanently and then go forward from there to fix and improve things with me.What I learned is that a small guy isn't looking for the perfect job to jump in and send 10 guys to.

@Henry Thomas Austin trailer homes can be much more difficult to obtain financing on because many times they are not on a permanent foundation especially as an investment property I would make sure your lender is on board with this before taking time out of everyone's day to look at the property

I am talking about placing a factory built home on a permanent foundation with that home built to the same national standards as used for traditional stick built homes.