There is a little science behind the up front processing to avoid UW issues.At the end of the day Vacation homes can still be rented out so it offers a 2 sided coin. 

Just get a proper home inspection and investigate the basement quality, electric type (i.e. knob and tube, aluminum, ungrounded, modern romex), plumbing type (i.e. cast iron, galvanized, pvc), and just be overall ok with an older building material.

It's easy to pass them all by and find one with amazing ocean views and bad decor, or better yet a STR with modern decor and close to the ocean.

My wife found some mid century modern chairs from Walmart but they were fabric and I’m sure they won’t hold up.  

New modern lights and ceiling fans, quality furniture, Big screen TVs (not so expensive anymore), big washer and dryer, one of those cool refrigerators.If you ever go stay in a nice hotel or nice airbnbs, try to pick up on some of the things they do to make it feel luxurious. 

Wanted to get buildings with more modern amenities, more up to date, and more appealing to people today.7.

This is easy with any modern cell phone.

The modern vacation rental guest has evolved, and their expectations have become more sophisticated.

More modern amenities and infrastructure and upgrading of restaurants, homes and businesses to support the influx of travelers, second home buyers and relocation of families and retirees. 

Per this NY Times article, the average American knows around 600 people.https://www.nytimes.com/2013/02/19/science/the-average-american-knows-how-many-people.html#:~:text=The%20average%20American%20knows%20about,do%20you%20know%20named%20Kevin%3FPer the US Census Bureau, the average American moves 11.7 time in their life, which based upon an approximate lifespan of 84 years, works out to be about every 7 years.https://www.census.gov/topics/population/migration/guidance/calculating-migration-expectancy.html#:~:text=Using%202007%20ACS%20data%2C%20it,one%20move%20per%20single%20yearSo, if the average American knows 600 people and they each move about every 7 years, that means that the average American knows around 85 people that move in any given year.How many of those moves do you want to be involved in?