Experienced Advice Needed On Next Steps

[Robert Carney]

I'm trying to kickstart my RE investing and have been non stop in books, podcasts, youtube videos, etc but still have reservations on my next move - curious what successful investors would do.

I have a condo that I bought and lived in with goals of being a rental, which has now has been rented since 2017. I paid $165k for it, put 20% down at the time. This is in a VERY desirable area of Tampa and has appreciated to the current value of around $350-375k. I currently owe around $100k on it. After property management, mortgage and everything else it's cash flowing a few hundred a month.

With the state of Tampa real estate these days, I have a hard time letting this one go but I'm focused on growing my portfolio. The problem is I can't seem to find anything that makes sense financially on MLS and work a full time job that won't allow me to do a full BRRR - i would be open to a cosmetic update but not complete overhaul.

I also have a young family so the fear of becoming over leveraged worries me. Over the years I've gone back and forth with the idea of 5-10 completely paid for rentals being my goal vs 20+ leveraged. I know most of this group would say that's the wrong strategy and I think I would probably be best suited doing something between the two strategies.

Do you keep the condo and just look towards the next property or do you 1039 it into a 3-4 unit mulitfamily which are also very difficult to find these days? Or something else?