For example, if a property is clearly a rental, does that typically have a higher chance of success?

If the developer that you're partnering with has experience doing similar deals, then there's a good chance that they have construction expertise and easy access to deals. 

I'd go ahead and list it.There are many past posts on how to improve your search list placement such as making frequent changes to listing and updating pictures.

A general rule of thumb though (not a hard rule) is that if a market has a prolonged history of vacation rentals such as towns whose commerce is very dependent on tourism like beach or mountain towns, then there is a good chance than those towns have established their airBNB regulations decades ago and are likely stable.

I know this sounds a bit like a weather forecast - "Sunny with a chance of rain" - but my crystal ball seems to be on the fritz right now.Best regards, Stevan

Chances are your unit will look like that when they are done. 

We discovered the previous owner had dementia which explained most of the work we needed to do, Our short-term is improving that unit to rental standard, not necessarily adding property value as he and I are still drawing floor plans for Long term.Thank you!!!

Before listing it on an STR platform, I need to make some improvements to my current home.How can I maximize tax write-offs for these improvements?

I had purposefully waited as long as I could in case it was blocked, but I figured chances were slim at this point. 

We don't do closets for better air flow and less chance of mold.