It's a smaller market, than the other bigger cities, so I've had trouble getting any examples.

Preferably one that is already zoned for business/tourism like my Disney property.You're just asking for trouble otherwise.

I've got about $10k I'm willing to spend, and here's what I've come up with as far as updates go:- Add shelving for grocery storage - there's very little today- Rehab the front porch (you can feel the plywood sink in places as you walk over it)- Repaint the outside of the house (paint is peeling)- Add a fence for the back yard- Add a back door (there's only one entrance/exit to the house)- Pave the driveway on both sides of the tree out front- Add exterior lights to the side and back of house- Update kitchen counters (granite?)

You are having trouble renting; REALLY?

And this means the deed must be allocated appropriately between the tic owners.If you're buying the property under your name and are trying to get primary residence financing that is where you may have trouble with the lender. 

One of my best short term rentals ever was a flip that I had trouble selling.

I hope to God you thought about your investment strategy and structure before you decided to say hey I love risk and lets just swing for the fences. 

The trouble on my mind comes down to monthly payment.

The trouble I'm having is what the ownership structure of Operator should be.

Slap some paint and clean them up sell at slightly below market - or new kitchen, bath and flooring which will cost around 50k each and swing for the fences?