I do enjoy underwriting and researching deals a lot, so I would welcome that part of it.

Is that the only asset class that you enjoy now?

Enjoy  https://www.biggerpockets.com/guides/brrrr-method

You have to enjoy and reward yourself sometimes.

As a SFR investor for over 15 years I have been wrestling with this question in the past, because it feels like you should upgrade to "bigger".I know for sure that I would not enjoy the ownership experience that comes with a small 4F, because in Milwaukee that typically also means lower income tenants. 

I will also add that many independent travelers that do room rentals enjoy having their own fridge.To keep things kosher in shared spaces, my friend who runs PadSplit says every room comes with one colors or plates cups etc to ensure that guests are accountable for their own dishes.

If you ever want to talk or go over some other options feel free to reach out or send me an email, I enjoy helping!

I definitely enjoyed this thread, which is odd since I don’t have a short term rental, but I guess a good argument can keep a reader in suspense.

I would have focused on the highest paying W2 I could find/achieve as early as possible in a field I enjoyed;2.

., more than half of the calendar year) for the Borrower’s personal use and enjoyment"This means that you can only book it out on STR platforms for half of the year (50% max occupancy), which really sets a cap on your max income.