I love the mountains, skiing outdoors, trail running (Colorado) and I love warm weather in the hard Winter (San Diego) so I designed my life to live in both place (god bless real estate:-). 

I keep getting dinged with new taxes, LLC fees, furniture replacement and kitchen item replacements.

Limit is 3 let’s per stay, and no pets on the beds/furniture or in the pool (yes, I have to specify this)

So far less than $5,000 to furnish a two bedroom condo including new furniture. 

You can upgrade other things.A nice outdoor entertain area is a big plus.

Maybe she just wants to pound nails, or move furniture, or pick out colors BUT she might want to have her hand in the financial details from day 1.Have that conversation with her from the first moment you think about going into business together.  

From my limited experience, if you decide to rent per room (as opposed to entire place) I would suggest trying to set up some sort of outdoor area.

Quasi-Luxury Short Term Rental. 3 bedrooms, 3 bathrooms, outdoor shower, private beach sand, hammock, outdoor built-in grill with range and mini fridge, outdoor gazebo with TV entertainment, and much more...

Many of my customers do this for a number of reasons: You're already looking to furnish the property for yourselfIt's a 2nd hours so it's an investment propertyYou can Cost Segregate all of the furniture, updates & upgrades you make to the property so your family can enjoy a nicer 2nd homeWhile you're not there, it's generating revenue and being professionally cleaned a few times a weekIt's an asset not a liability If you're new to Cost Segregation, here's a BP Article: https://www.biggerpockets.com/blog/real-estate-investors-pay-attention-cost-segregation/Also as you're searching properties and you want to know what type of returns they could create, you can submit them to Hoasty.co and it will send you a free AirDNA report of the potential earnings going forward. 

Require all tenant-owned furniture to have padded or nylon foot pads.