I also  plan on doing a check in check out sheet similar to that of our long term rental in case any damages they would be liable as well.   

I plan to research more on the MTR space.

I've tried a lot of products, and haven't found quite the right fit.

The exercise of tracking it regularly helps to keep it top of mind and it also allows me to see how my plans are working compared to my goals and if I need to make adjustments (I agree with @Chris Clothier that you've got a keep a long-term perspective because real estate investing, like life in general, is a marathon not a sprint).Great question, Allan!

Seems like this would make a great business plan if it was even possible

Rented my house we originally lived in 12 years ago because we couldn’t sell it when we moved and that’s how we got started. 5 years ago we made a plan and an effort to accumulate multi family properties and did that.

Yes, I am planning to follow the rules for the STR loophole to go against my W-2 income.Has anyone performed a cost seg in this area?

Getting into a property that has negative cash flow can seriously hurt, even if you've thought out a magnificent plan for it.

However, the good news is that there are other planning options available where you don't need a real estate license.

Planning to buy another primary in a year or so!