And looking for challenging, yet simply convenient ways to enter in/build a portfolio.

I manage 25 furnished homes in the San Francisco Bay Area, and I focus on business travelers seeking value and convenience for 30+ day stays (with some STRs mixed in).

Absolutely - then again, when is it a convenient time?

The only 2 things that "might" change a guest's mind toward your place on that list are the smart locks which is just a convenience factor because they don't have to go see anyone to check in and don't need to keep track of a key, and the security camera, just for peace of mind like someone else mentioned.  

CON- It's a gamble & if your timeline for returns is short then it may not be worth the risk.

Just like a gas station that also has a convenience store, like a parking garage in a city.    

Let me know what's most convenient for you and how to connect offline.

Has the neighborhood improved or is it a huge gamble still?   

This is because short-term rentals are typically priced at a premium due to their flexibility and convenience for travelers.2.

While finding a lake house that is close in proximity is convenient as far as maintaining it is concerned, the price may be too high or the return may not be as much as you'd like.