Advise for managing property of out of state

[Donald Aleshire]

Hello, wanted to get peoples thoughts on long distance rentals and how I should best prepare --

I have two 3 unit buildings in Chicago that I have owned for several years. We started house hacking back in 2018 and lived in one unit for 5 years. Prior to our first son being born, we purchased a second 3 unit building and currently house hacking that for the past 2 years. 6 units in total with us living in 1 of the units today. All long term tenants with 0 turn over (so far). My rents are a bit below market rate but no tenant turnover is nice.

My wife and I are looking to move out of Chicago to San Diego in the next 12-18 months. We are currently making roughly $1k per month house hacking all units and would earn a bit over $4k per month with all 6 units + garage spots rented out (Rental income - PITI). Total value of the 2 properties is roughly $1.5M and I have close to $600k in equity.

The buildings are both 100+ years old but I have done my best to do capital improvements over the past several years. Updating pipes, electrical boxes, roofs, appliances, etc. I also have a good network of people I trust (electricians, plumbers, painters, roofers, etc) but I do not have a reliable handy man. I typically do most small jobs myself or find random handymen who do a decent/poor job.

All leasing/property management is done by me today and I think it will remain that way in the future, even from afar. I would farm out my local friends/baby sisters to help do showings if a vacant unit arrises. I also thought about leveraging my Chicago network (friends + neighbors) to keep an eye out of the properties from time to time. All tenant issues would still come directly to me via text/email/call and I can be the middle man to broker the communication with handyman/repairs/etc.

I have handled issues remotely before in the past while on vacation for a few weeks (pipe burst, sink clogs, broken appliances, etc.) While not fun, I have managed to get through the issues and returned home to everything being solved.

My biggest challenge is finding a handyman I can trust for simple/small/medium jobs. How have you found handymen in the past? Where have you found success finding them? Any details you can provide would be helpful.

Since I have the next 12 months to plan for this, I am open to any additional feedback/suggestions on what else I should think about. Based on the cashflow, I think it makes sense to hold onto these versus sell but again, open to ideas. Thanks!