We are only very moderately leveraged, but I am in no rush to change that and rather use the cash flow to re-invest either into upgrades (we are doing a ton of driveways this year) or more RE.I don't think there is a right or wrong way, like you said there are many different ways, I just find myself adjusting every year a bit more in that direction. most condos historically are not great appreciation plays. its a place to live and enjoy.. unless said condo was bought in Miami in 2008 to 2010 :)No $#@% mate.And Chicago has been a disaster for many years now.I pinged Bri about it a while ago and she said "Good luck" hahaI guess it's more a trophy property than anything else during my "ego" pumping days.A bit older, balder and smarter nowadays I guess.Less is more mate lol

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

I enjoy learning and growing as an entrepreneur, investor, business owner, and person.

., 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. 

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.