I love this community and feel like I have learned so much from it. Just got into house flipping / real estate investing a few years ago, and have so far done really well (and also gotten extremely lucky) and it seems like right now the consensus on this sub is the biggest mistake folks feel like they have made is attempting to time the market or not investing within the last few years despite having the ability to do so. But I feel like my experiences are biased by…my own experiences…..which only started a few years ago.

As someone who is still very new and is constantly trying to learn from those who are more experienced- I also feel like the best way to learn is from your mistakes.

What’s something that you did within the real estate space that you consider to now be an “unsuccessful” move or a “mistake” or something you wished you didn’t do?

Some of my mistakes:

1. Being honest about my lack of knowledge with contractors and being someone that is really really “nice” where I’m easily gaslight into paying early (happened once, home boy took the money bailed, never again). As with anything, some are honest and some see it as a solid opening to take advantage of me. I now learn, do research, and do my best to know exactly what I’m talking about and get many quotes before I get something done. I also aspire to be the kind of person that knows a lot more about general “fixing” stuff. I feel like I have already made strides from where I was a few years ago but I want to be better.
2. Worrying too much about things that aren’t really in my hands and trying to get the “best deal” but not balancing that with how much better the deal will be once it’s in my hands. Without necessarily offering what I would actually pay. It’s happened twice, where I lost out on two great deals over only a few thousand dollars that I absolutely would have paid had I known and had I just went with what I would have paid in the first place, it would have happened. Hindsight sort of things
3. Ignoring red flags with tenants because I felt bad. I want to be the kind of person that helps where I can, and in some instances I have had good luck with it where I took a chance on someone and they didn’t screw me over…..but I recently am dealing with a situation where I knew 100 percent right from the get go that it would end badly (I didn’t anticipate just HOW bad though) but I felt horrible for them and their situation and wanted to give them a chance. And I didn’t have to. I had a list of solid potential tenants, but just felt really bad. Not only did it end badly in the ways I expected, but they caused way WAY more property damage than I even thought was possible, in addition to an ungodly hoard, and of course not paying for anything. It wasn’t worth it. There may come a time when I’ll be in a situation to take those risks because it can help someone else, now is not that time.

This whole thing hurt me so much more than it should have. Lots of lessons learned there unfortunately. I won’t ever hate someone for not being able to pay rent because I know that stuff can happen and I’ll always do everything I can to work with you and the situation, but if you’re going to ignore every single attempt to even speak to me and tell me what’s going on,and then destroy property in a way that is completely unnecessary and is only possible through severe carelessness, I don’t even know what to tell you.

4) Definitely lots of missed opportunities. We recently missed one that I wasn’t able to make the funds work for (off market), and it was finally put on the market months later as is for 400k more than the price we negotiated and went pending immediately. Looking back I wished I had tried even harder to somehow just make it work . I literally printed out a photo of it and have it pinned up as motivation lol.