Are there tools or rules to estimate the expenses. 

If you decide to revisit STRs, you might want to explore properties where you can project expenses independently, such as using local STR forums or online tools to estimate maintenance, management, and occupancy costs.For networking and strategy-building, you might find local meetups or groups beneficial.

It looks like Privy is a great tool for identifying investment properties by using up to date MLS data.

Tools like BiggerPockets Calculators and rent estimation tools are incredibly helpful.

Both strategies are great and have their pros and consOne of the biggest wealth building tools in real estate is the ability to purchase a property as a primary residence and put less then 20% down.

I feel like in today’s day in age there are so many tools for STR operations and I cannot believe there is no integration for a merchant of sale transaction or some kind of financial app/ software that can take the remitted taxes and pay them to the government automatically.

They might be lower than anticipated and are a great tool for what you are looking to do.

Any other automation tools you suggest ? 

Are there specific metrics or tools you rely on?

You also have to be super detail-oriented, focused on continuous improvement regarding the property and guest experience, very in-touch with what it's like to be a guest at the property (and a cleaner of it as well), and focused on technological tools and opportunities.