@Tuesday Goodband
I am not an owner occupant but live within 15-20 minutes of the properties. All of them were vacant at closing. One is a SFH that required some "sweat equity," and the other is a triplex that was "good to go". Fixing up one property and filling four units was a TON of work.
I tried to save money during the renovations via DYI but it took longer than having hired help. Additionally, there was no rent coming in. Analyze your numbers and determine what works for your situation.
Closing of the triplex was towards the end of summer, the vacancy of the last unit in this building did not get filled until November. Winter was coming, interest in the dwelling was limited and I settled on a applicant. DO NOT DO THIS!!! Needless to say, the tenant is no longer with us and I am using this time to improve the apartment. I WILL have an A+ tenant next time around.
I do not use a property management company and perform the work or hire it out myself. Although, I am trying to move away from doing it myself. Making connections with handymen has been the most difficult task yet but I may have found one. He is a referral from a fellow landlord that we came into contact with while screening tenants.
These are all the negatives we've had to date but there were many other things done correctly. To start I would say learn how to analyze the financials of a property and find a real estate agent that focuses on investment properties.