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? 

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.

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

If that is the case, just let them take it to market to sell.You could offer to manage the property and have them to rent it out now where you pay them a flat rate every month and anything you make over that amount is yours to keep.

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.

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

If so, this serves as a great example of how much the market has changed - if someone were to buy this property in 2025, it would have significant negative cash flow, whereas you have positive cash flow given the price point of purchase in 2021.  

While we are not immune to market shifts, we typically don't see huge bubble bursts. 

Very communicative, hands on, and thorough with their property management.As some additional context, I own a few rentals in different markets and Michele's team is top notch compared to them.

What market are you referencing?