In addition, while the umbrella did not end up having to pay out, having it meant I did not stress about it at all.  

At the end of the day if you run your numbers and analyze like 10 properties a day, and every single day scour the internet for anything new, you will eventually find something that works and know it almost immediately.

Many of my clients are high W2 earners who are taking advantage of the "STR loophole." 

I have googled it and it takes me to links that are too broad and end up as a dead end. 

Focus on high-demand rental areas (suburbs for multifamily, tourist/business hubs for STRs) and consider scaling with the BRRRR method to build passive income.

Highly recommend.

Quote from @Jimmy Rojas: I live in Arizona and homes here are sky high, youd be lucky to get %6 interest rate, I would be a 1st time home buyer, apart from being 1099 employed would Trumps real estate plans benefit the little guys like me? 

The only exception I use is when the property is a high-end unit.Informative title makes your property look like a cheap business but it is still way better than common titles like cute, adorable, cozy.If you are charging over 1k per night, I think it is better to give more high-end title like Stay with 30,000 trees, tingle your inner artist with lake front retreatJust my opinion :)

@Micah Huffman unless you are going to commit to learning some basics about being a landlord AND are willing to commit at least 2-4 hours each month managing a Property Management Company - it's probably best you sell.Otherwise, it's highly likely you could lose more due to bad tenants and management.

They have to be tweaked on a regular bases and most of the time it is due to it throwing out some crazy high ridiculous prices for some dates.