She informed me that she & her sisters plan to take care of the rent so he still has the home when he gets out of the hospital. 

Please feel free to reach out to me and my team if you would like to come up with a game plan and build your buy box. 

We also just purchased a house in Oliver, WI that we plan to run as a short-term rental.

I am just starting out with a STR and found that VRBO is not very specific if they are collecting the tax and paying it to the State as a marketplace facilitator or am I responsible for this tax collection and payment ?

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

What is your plan to obtain this dream?

very high risk even I only do them with very specific investors in mind and a plan. we dont flip land we develop every one. 

But, since you seem to be implying very specific things, but without being specific.

Sometimes it makes sense to have a back up plan for a DST. 

.: @Srikanth Kumarjust curious how you plan to manage a BRRRR from out of state.