You could easily lose lots of money and time with a contractor. 

I did not look out for the special assessment but was purchasing from a wholesaler and did not want to lose out on my down payment.

And what are the tax implications if I make money/if I lose money at the end of the year?

Our strategy of taking underperforming multifamily properties and converting to top performing STR units with automation and streamlining would work well in the right hotel setting in my mind, especially with it being an invisible-service structure, and not needing office space or on-sight staff, and everything through an A la carte platform.

I just want to get my feet wet and want to learn and not lose tons of money.  

Always worth the search, so your cash isn't losing value with the banks current sub 1% interest they give you!

Hopefully you are cash-flow positive on the property.The property will gain or lose value over time.Are you happy with the cash-flow and appreciation?

After many years in property management, my experience is that holding a D property as a long-term rental will lose you money, IMHO.

All of a sudden the world looks different, 1000's are losing their job, 1000's are dying, lending slows down, deals start to fall apart.

I was able to get the new lot free and clear off the main house and not lose any value on the house either.