How do you handle these situations.

Determine how comfortable you are with potentially locking up assets for a long time and how much risk you can tolerate.Market Conditions: The situation of the real estate market might change, and this could have an impact on your choice.

You cannot necessarily expect that the situation in the summer of 24 will be exactly the same as it is today.

From my understanding, if its passive income, just a room-by-room rental, it would go on your schedule E just like any other rental. if its active, like a short term rental situation or mid-term, something like an airbnb or bed and breakfast where you're actively including extras, it would be filed on a schedule C. disclaimer, im not a tax person, so double check this with your tax pro. when you go to qualify for your next purchase, whether that's for primary or inv., using a full-doc loan... if its schedule C, you would need to do a 2 year average of this income in order to use it. its looked at as a business, and self employment income. if its schedule E, theoretically you could use the schedule E income calculations just like any other rental even after the first filing.

Adam,I am sorry to hear about the tough situation!

You can't know how a deal structure will impact the seller's tax liability without knowing their whole financial situation. 

Can you please share your experience buying or passing in a situation like this?

I agree, oil covers more, ugly if you use it over water based paint though.Well, given this situation, wouldn't you really want to remove the water based paint first, so the wood itself gets treated with the odor removal products?

This is the situation we are facing coming up.

Its a very strange situation, I see lake fronts charging 400-500 in the summer which is understandable so I as well as the others in the area without it charge $190-250.Now like I said many of the one bedrooms in the area are not up to the standard that mine is and have bad occupancy at $140 a night in the slow season but I did find a property which is farther off the water and a few neighborhoods over that charged $275 a night and is pretty packed but no better than the $140 ones.