I'll remove appreciation from my base case scenario since it's speculative.

@Allan Smith ah, the age-old cashflow vs. appreciation debate...where one stands on this debate should depend on their financial picture.A 20 yr old kid with no net worth can't afford to break even month to month on their first property, and they can't afford the risk of speculation on future appreciation...that's too much risk for them because they have nothing to protect themselves when things turn south. 

However, making investment decisions based solely on predictions or speculation can be challenging.

I’ve got $20k in reserves in a high yield savings account, plus the usual mix of speculative crypto and blue chip IRA. 

Using your savings as a down payment to buy something that may appreciate more in the future and attract higher-quality tenants.I wouldn't buy anything with the speculation it'll appreciate, but there should be something better available than a 2/2 in Sunnyslope.

My speculation is that you can file an LLC. 

I have extra money that I am not afraid of losing so I throw it in to some stocks based on speculation.

But "cashflow is king", and "appreciation is speculating"...   

I assume the home is in a Cleveland suburb so I speculate it isn't appreciating as fast as the loss.If bleeding money is ok, how long should it occur?

I don't know how to assess future appreciation - all arguments seem highly speculative at this point.