I guess it can save you some time managing, for example one tax bill, one insurance bill. 

Quote from @Jay Hinrichs: Quote from @Sam Wilson: We invested via a retirement account.

The point of the contract is to provide value to both buyers and sellers and  this deal saves the buyer over $1M in interest and easily $100k in furnishings while getting the seller their full equity and saving buy side/sale side realtor commissions.

2021 hit and that is when I became financially free and was able to retire from teaching at 55 yrs old.

Setting up direct bookings is a great way to save on fees, but you’re right—it requires extra effort to ensure everything runs smoothly.For vetting guests, start by asking a few questions when they inquire, like the purpose of their stay, how many people will be there, and if they’ve stayed in short-term rentals before.

First house was a house hack, so saved me a big chuck right off the bat. 

Suggest you pester them with questions to learn the eviction process, so you can save money in the future.

Or just keep renting and saving in San Diego where we're familiar with the area and the market (which could take awhile, while we are probably 3ish years away from investing in a Midwest market).

We will both keep our W2 employment for the near future just looking into getting an extra income or make our retirement easier.

Get on a budget, build your emergency fund, pay off all debts, save up.