Fairmont is a good little market!

We don't want to bring on every owner or every property unless they fit within our target market, so, I do the far majority of the sales - this is our check and balance.

But, the self-sufficiency test for FHA loans can be really difficult in SF, meaning that the market rent from units you will not occupy must be sufficient to pay for the mortgage payment. 

When I worked with a property management company, we had someone buy a unit (single family) that had a STR and marketed it as a STR.

If we are losing money every year, but do plan on holding on to it long term, with our goal being appreciation of the market and someone else paying a good chunk of our mortgage, is this worth doing on any level? 

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

Here are the markets I’m exploring:St.

Obtain a working knowledge of the local rental market. 

My thinking is I can not as it probably works as I does in the stock market with my IRA.

You should start with a focus on a 2 unit multifamily property in a market that you can afford to get into.