You’ll get clobbered because big ticket items needing to be replaced and occasional updating or make ready turnovers between tenants will cost you many thousands.

I'm looking at condos that are part of hotels/resorts, for occasional personal use (I travel a lot and need a place to come back to), and to have STR income when I'm away.

Paula Pant also has a good perspective on the topic and touches on it occasionally in her podcast, Afford Anything.

Refi puts about $17K in our pockets now but literally EVERYTHING is new so it shouldn't need much except the occasional repairs here and there.  2) The property sits on a double lot. 

Some of the owners in that area own a dozen or more houses and occasionally sell them off in packages.

These days, I buy notes occasionally, but only when the case is already filed and completed. 

We know that houses are going to need a furnace/roof/hot water heater occasionally.

I’m thinking about luxury condos for short term rentals since I’d occasionally want to have a place I can use for myself.With mortgage rates so high and HOA fees for many of these buildings at around $1k a month, it seems like investing in a condo in Miami is more of a game of price speculation.

And many are the ones you are reading about in the news (or soon will) as they lose properties to foreclosure and wind their way through civil (and occasionally criminal) court.  

For example asking for minor upgrades to the unit but in a way that blurs the relationship boundaries.