I’d like to work towards making a trip next year, it’d be awesome to time it up with a local meeting.

Then the 4X/year you go there on "maintenance and inspection" trips are business related and tax deductible.

But my heart wants me to invest in Big Bear Lake so I can take advantage of the thriving Air Bnb market there, as well as have a ski trip getaway every now and then.

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I take about 4 trips home a year and it only gets scary now between tenants(if they don’t renew), but your team of handymen, landscapers and relationship with long term tenants are the key to it all.

I made a countless trips to Home Depot and Lowe's because I didn't have enough materials or bought the wrong ones.

I've literally made one trip to the office and asked as many questions as possible within my limited time there due to other engagements. 

It’s nice to see the old world character with the walls panels and so on.

Poorly done concrete becomes a trip hazard3.

On the other hand you’ll have a reliable tenant in dad, property taxes are low, insurance is low, and you can probably make a tax deductible trip to visit dad each year (confirm that with your tax person).