I hope to retire after 32 yrs in my job, on or about January 2021. I will get a defined benefits pension. Kicking around open ended ways to supplement that. I have a significant amount of savings which I could tap into to buy some properties. Not interested in being a landlord, too much hassle these days with dead beat tenants and damage, etc. However, I am currently in the process of flipping a small condo locally in town which I'd bought in 2015 for son and daughter-in-law to stay in for a year as tenants while they get their ducks in a row. Well 1 yr turned into 4 and they've finally moved out and bought a house. However, as the saying goes, "No good deed goes unpunished" they left the condo in extremely dirty condition and with some damage. Pretty much as if it'd been standard issue non-family tenants living there who didn't give a hoot. I realize it was a mistake now but at the time I wanted to help out since his mother had (at that time) killed herself a couple yrs before and it'd been a tough time for all. So as they say, I've now chosen to make lemons into lemonade of the situation and instead of brooding about the disrespect of my generosity providing a rent free place to live for 4 yrs to them and they more or less trash it, I'm instead looking at it as a Property Flip training event. I'm friends with a Realtor who's a top producer w/ 15 yrs experience and has a ton of contractor contacts for rehabbing properties in all sorts of conditions. I've done some light work in it myself but contracted out complete re-paint, new flooring for approx 2/3 of the floor space (tile & grout in remaining 1/3 cleaned up good). Bought it for 76K cash in 2015 (was listed @ 85) and Realtor is pricing 109K for this week's listing, and selling on a reduced commission. New stainless appliances and a new high efficiency heat pump in combo with the other work and I have put about 10K into it to bring it into Like New condition inside. And being a condo the outside is covered by the Association. it was never about making a big profit on it in the first place but it has fallen into place a small low end flip, and to be honest it's not been too bad, just time consuming getting the painting done as it was a guy I work with who moonlights painting who hooked me up cost wise but trade off was slow completion. Worth the wait for the discount plus the finished work looks good including numerous drywall repairs. So long story short, it's made me start kicking around the concept of flipping properties for retirement income supplementation. The real estate market here is cheap always has been compared to other areas of the nation, as a yardstick consider that this condo is 1050 sq ft two br two full bath eat-in kitchen but spacious living room with four parking spaces (yes four but non-enclosed parking), and consider that 109K is what the Realtor came up with given recent comparisons and the new paint, carpet, appliances, hvac. Elsewhere in the nation likely be higher valuation. But because you can buy cheap here, flipping might be a workable income supplement. I have to think about it.