I’d love to hear from fellow self-managing landlords about the biggest lessons you’ve learned along the way—whether it’s handling difficult move outs, maintenance strategies, or unique ways to streamline day-to-day operations.

As someone who's spent the past 20 years building software to ingest massive amounts of random data, the short answer is, it's really difficult to get accurate contact data.

It's very cheap and not difficult to maintain bond/license/insurance.

These can make crunching numbers a bit more difficult because due to the guessing game. 

In terms of STR it seems that in the really strong markets (Lisbon, Porto, old town Ericeira) it is difficult to get the AL licencing.

The town of Speedway itself is difficult because of the price points, but it has a really good ROI. 

Don't hate it, embrace it and enjoy other parts of life.Also making $575k/annually in 5-10 years as a goal with $500k cash deployable today is just difficult and unrealistic. 

In all honesty, it will be difficult to collect anything from the tenant after they move out and you cannot force them to stay.

If they are difficult, the current landlord may not give you a straight answer because they want them to find a place and move out.

Quote from @Jacob Hrip: I’d like to begin my real estate investing career in 2025.