From what I’ve seen, the value of a premium listing really depends on a couple of factors: the local market's activity and how saturated it is with similar rentals.

For the 1/2 BR you are competing not only with other STR's but also in a sense hotels.4 - The Tall Timbers being STR friendly will this cause saturation with a bunch of new units coming available in the same development?

It has become more saturated as STR was shut off people switched to the MTR strategy so have LTR as a backup if it does not workout. 

Think the puck stops with you trying to be some form of leader on here.Self proclaimed "Zen" of Real Estate, give me a fat ****ing break. 

Best Starter Markets: For investors just starting, which cities tend to have good entry-level opportunities for multi-family units but aren’t too saturated or risky?

It's near most Ohio markets but is far less saturated.

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I am wondering if anyone has experience in the short term rental market in the area being too saturated?

Overall, it's a great idea/theory, but execution has gotten much more difficult between regulation and market saturation in some more popular areas.

Tangentially, there are a fair amount of former STRs now being sold around town in part because of the regs and also saturation.