The addition of a private balcony and standout interior design further elevated its appeal to both short-term and long-term tenants.

In addition, if you are buying in a remote market its appropriate to budget another 10% for property management.

You might also consider forming an LLC to manage the property-related business activities while holding the property in your name to stay within your lender’s requirements.Explore safer rental strategies: If you’re open to short-term rentals, Airbnb’s Host Guarantee provides additional liability coverage, which may offer peace of mind while keeping the property in your name.

Determine how much money would be needed to handle each risk, and determine if you have sufficient liquidity / cash flow to ensure you can “stay in the game”.This is of course in addition to all normal “due diligence”, financial forecasting, etc. 

Additionally you have to be ok with not disclosing your true intentions as for the use of the information.

If you have the other income and can afford to keep rolling your RE profits and additional money into growing your RE empire for the long term then there is no rule saying that you shouldn't or can't do that.

The farm is also permitted under the "dude ranch" CUP to build additional cabins or smaller buildings to use as short term rentals, or worker housing, or other options.

We chose this timing because 1) there was less chance of additional issues making the refund seem inadequate, and 2) it created a positive impression right before guests were likely to leave a review.

Additionally, if anyone has recommendations for a good CPA or attorney familiar with real estate and landlord-tenant laws in Oregon, I’d love to hear them!

That might offer additional peace of mind.