Sold my triplex and severely regret it. Can't get over it. Extremely depressed.

[Account Closed]

This post will likely make me sound like a total moron, and I accept that. I'm making this post as a means to vent, and hopefully get some perspective from others who may have been in a similar situation in the past and how they have moved forward.

Back in July of 2024, I lost a bunch of money in the stock market by being an impatient **** and not maintaining and holding onto my original investment, by self doubting, I sold a winning opportunity for a sizable loss of 30k, and then immediately lost another 100k on a stock I told myself to avoid. AI hype was reaching popping point which was my thesis for buying MCD call options, which were severely underpriced and I foresaw MCD flying high and producing 250-400k profit in a relatively short duration of time. 

My self doubt creeped in and I overwatched the charts, I didn't listen to myself and simply place take profit orders like I had originally planned to do. In the end I ****ed up and lost 130k in damn near 20 days, by ****ing up like two or three weeks before MCD finally moved upwards. This situation caused me to become extremely depressed and apathetic.

At the time I was the owner and operator of a triplex I had owned for just about 2 years. In that time, the rents had flown upwards. The triplex is a 2 bed 1 bath x 3 units. I lived in one unit and rented out the others. The rents were $1000 each when I bought it, and I quickly raised them to $1350 each. and then a year in I raised one tenant to $1500 and left the other at $1350. With the spare bedroom in my unit, I was able to pull in another $800 a month and use that to basically pay all my bills.

This one property paid all my living expenses when it was fully rented. I had solid long term tenants who didn't cause me much issues at all.I was effectively retired and out of the rat race, though living modestly in a house in the "hood" to achieve that financial freedom. But regardless, I need a place to live and money coming in, so it makes sense to own that property.

Anyhow, I lost a bunch of money in the stock market rapidly, simultaneously was taunted by the reality of how right I was, my prediction of this going up to this price per share and producing ~$300k+ profit, and avoid this because it'll implode was so right, it broke my mind and spirit honestly.

Simultaneously while this was occurring, my tenants suddenly had random **** for me to fix. I took care of those issues though they were inconvenient and annoying, that's part of the business. When I say I was depressed during all this, I mean it, I physically didn't even want to stand, I had burnt 6 months of hard work, and missed out on an opportunity that would have allowed me to finally have some more money and options, I intended to take the profit and buy another property in a nicer area, and rent out spare bedrooms/units and finally be able to bump up my passive income (my only stable and definitive income) up to $2000+ a month. I was excited at that prospect, excited to finally live somewhere nicer.

Well while I was in this depressed state, and just freshly dealt with those two issues from the tenants, I noticed some water damage in my own unit. My gut told me that the issue was caused by the tenant above me's window AC unit, draining improperly. Due to my apathetic and low energy, I didn't physically go up there and check myself. Big mistake. I texted the tenant asking them if the AC was leaking in my units due to improper installation. They said "nope I don't see any issue".

So I leave it, and go sleep over my moms house for a few days because I was feeling down and wanted to be around family. I come back two or three days later to get some extra clothes to stay a little longer at my moms. At the moment I was thinking and planning to find a roommate for my spare bedroom in my unit, so I could get some extra income while I buckled down and rebuilt my lost money from the stock situation. When I came back to my unit, I noticed the water damage had expanded substantially. I started to freak out because I couldn't figure out what was causing the damage. I started to worry if the pipes in the house had burst and that I would now be stuck with thousands in damages and repairs.

So i call a plumber to help me figure it out. He stops by for 2 minutes and checks the basement and then says "nope its not a plumbing issue". I was relieved because I knew it wasnt a huge issue or costly mistake at least. But I still didn't know what was causing the damage. I asked him who I need to call to figure this out then, this jack *** plumber is walking out the door after 2 minutes of being there, and charged me $150 to come check out the situation, and didn't even take a second to help a brother out with figuring out the issue. $150, a total rip off, that I only agreed to because I was just trying to figure out this **** before it got worse. The plumber tells me to call a general contractor instead of helping me figure it out.

I'm running on low sleep during all of this ******** occurrence. Questioning God for letting all of this happen at once and so perfectly self sabotaged myself. Questioning myself for ****ing myself, even though I had been so confident in my investments and the outcomes I was anticipating. 

Anyways I go on facebook real estate group page and share a photo of the issue and request a GC's help with figuring out the issue and fixing the wall. I get a quote of $5000 from one guy, which was absolutely insane and asinine. Another GC quotes me $650. Which was still expensive relative to the request I made but I was willing to spend the money to have someone take this ******** off my plate so that I can get back to finding a roommate and getting that extra cash flow. 

While I'm getting bids, I reach out to the tenant again and re-ask them if their AC is leaking. This time they say it is and they fixed it... Great. At least thats figured out.

I forward this info to the GC who quoted $650, I have him stop by the following day so we can knock this out. He says itll take 3 days to complete. Which seemed reasonable based on my limited knowledge for repairing the wall. 

This ****ing guy ended up ripping down 3 plaster walls, ripping off the trim from two windows and a walk way, damaging the trim, rips the floorboard which ****s up a bunch of vinyl planks and they pop off the floor, caused a bunch of scratches and gaps in the vinyl planks, he handed me a fake contract and while i was distracted reviewing the document he rapidly damaged three walls which left me paralyzed and confused and just shocked overall. Couldn't believe the amount of bad luck that was occurring. Routine maintenance turning into a full blown project.

The guy ends up taking 3-4 weeks time to complete, he's a ****ing ******* the entire time, my cheap *** should have fired him and hired someone else, but the debris and work he produced was probably gonna cost me $5-10k now, instead of $500 it should have. My furniture and couch is now covered in so much dust, floors look like ****, I can't get a roommate, the summers coming to an end, less opportunities to find tenants for the spare room. I'm freaking out, not sure how to get out of the situation, it's just me, I tell my family about what's happening, they totally dismiss me the same way the contractor was gas lighting me the entire time acting like he's doing everything proper and acting like it's nothing. 

By the half way point I'm talking to my mom and basically ready to move in with her like she offered initially when I asked to sleep over her house for a few days, in fact I'm so frustrated, blaming my stock market **** up on the work I was distracted by with the house, I'm even ready to sell to avoid any more of this madness in the future. Freaking out and worrying if this old building will have crazy future capex, or if the RE market will crash like the stock market was briefly doing at that time. I start over thinking just like I did with the stocks **** up. Wondering if this is worth it anymore, am I just safer day trading and swing trading stocks with my equity?

As an overthinker, I started assuming the worst. Started questioning how safe RE is as an investment. By the time the contractor was done, the work was really ******, and it was basically september. I wanted to just go back to my house and go back to my life. I needed my mom to drive me back in her bigger car so I could bring my computer and desk which didnt fit in my car. I asked her 2 or 3 times, and she kept guilting me to stay with her.

I ended up somehow listing the property and throwing out half of my ****. I had it listed for a few hours, and then I canceled the listing and felt relief. I told my mom happily that i decided to keep the property and she casted further doubt "oh you're just gonna change your mind tomorrow". This made me wake up the next day in a panic attack, which led me to relist it. 7 days later my agent shook me into making a rash decision in the early morning without properly thinking things through and I accepted an offer. I ended up selling for 425k, 2 years prior purchased for 315k. My agent convinced me to give 2.5% commission to the buyers agent as well smh. 

As I had it listed I started to realize I could increase my rents and could have had $1500 rent, $1750 rent plus a roommate $850. After setting aside $300 a month for repairs, paid PITI and paid operating expenses, I would have been cash flowing $1150 a month!!! Which is plenty of money to survive comfortably for someone like myself. I could have been living my life, had all my stuff the way it was, money for repairs and paid for everything comfortably.

Now I'm stuck at my moms house. The thought of working some **** job 40 hours a week to get $60-70k a year, pay rent and bills to maybe make an extra $1000 a month is such a huge loss. It's been 8 months since this happened, every day I wake up so depressed and confused how everything came together like this. I did it to myself, and it hurts my soul. I feel like a shell of my former self. I wish I just followed through with all my original plans from holding MCD to keeping the house. 

Has anyone ever ****ed up this stupidly before? Has anyone ever felt like this before? 8 months of pure loss of plans and depression and demotivation, and I don't feel any better with each passing day. Having that property was key because it gave me independence, paid all my essential bills, and I had money to invest with which made me happy and allowed me to put extra money away and I looked at property management and investing in stocks as my occupation. I DONT KNOW WHAT TO DO ANYMORE. I lost my 5% interest rate. I can't find any cash flow even close to what I had. I can buy a house but be completely cash poor. Or I can risk money in the tumultuous markets and not have a house or steady flow of income from rents. I've ruined my life truly.