SF's market is still very nuanced and strong due to the low inventory and demand here, homes still going above ask with multiple offers. 

Evaluate the inventory: Take inventory of all your furniture, decor, and kitchenware.

Depending on where you are looking, inventory for 1-4 units can be a challenge as a lot of the NW suburbs are all single family homes unless you are further NW like Rockford or Elgin or something like that. 

Flat fee ranges from $299 to $1999 so there’s a large area in betweenThe very basic is a listing on the local MLS.  

It does feel like there is likely a major market correction coming, but due to limited inventory of vacation-rentable units in Maui I feel like I should be somewhat more protected from the effects of said recession.

However, upon research I have discovered it is really hard to find cash flowing HOUSES in good areas in my price range. 

The pandemic shook these age ranges for a loop so we are still seeing where their paths will take them.

<---if you own Jefferson County properties in this age range, this issue should receiving your attention. 

It’s great to see your post, sounds like you’re deeply involved in the real estate investing world with a range of strategies.

Yes, you do get income on the other side, but the prices have bumped up so with interest rates and less inventory to buy, the net income is much less than a few years ago.You can still do it, you just have to factor that in and expect negative cash flow while you live there and then see how good it will be when you leave in a year and do it again.