Like @Bruce Woodruff said you have to establish your goals and "why" REI or homeownership should be in your life.

That project taught him that buyers in these well-established neighborhoods pay close attention to the details..things like making sure the ceiling lines are clean, storage is intuitive, and every inch feels purposeful rather than tacked on.For your project, thinking about the functionality of the added space is key.

I get CC offers on LLCs I establish within months of launching them.

I started looking in surrounding areas and found that the markets less established or still rebuilding had much higher cap rates.

I'm a very analytical person who won't start a new venture without first gaining a solid understanding, establishing the right framework and connections, and ensuring that I'm securing a great deal.

These are very risk gambles that should only be attempted with money you don't really care about.  

In our experience that is what carries the day along with the area and the STR restrictions or lack thereof(a whole other conversation) that deems the valuations.Airbnb and VRBO have thought of this and are way ahead of it, we scaled quickly using these platforms for two high end STR that book out great, once we established that, we created a direct book website and are slowly pulling our repeats from that.

A terms sheet will tell a pro whether you know what you're talking about and give them a structure of the deal you propose, but it won't establish credibility with respect to your financial ability to pull off the deal.

For that time frame it would not make sense to turn it into a STR as there won't be enough time to establish a history to attract good vacationers.

In more established markets like Austin or Omaha.. from what I’ve heard in Bloomberg, guests value transparency as much as good rates.