What were your 1st and 2nd RE Transactions?

@Kirk R. found a house online in 2008, didn't even know the neighborhood as I had just relocated for work about 60 miles from where I grew up. I knew a local Realtor, and went to take a look. It was a full rehab, smelled like animal urine, the floor plan was obsolete, you get the picture. I had probably $1,000 in the bank, if that. The asking price was $79,900. A house across the street had just sold for $135,000. The Realtor told me there had been 94 showings, and no offers. I found a hard money lender who would loan 65% of the repaired value, at 16% plus 7 points (yikes!). Being naive, I jumped in head first. I ended up buying it for $62,000. Meaning I had maybe $20,000 to work with for repairs and it needed probably $35,000. I ended up spending WAY too long trying to do all the repairs myself. I hung 100 sheets of drywall in the cold of winter, after working 10 hours at my "real" job. I moved in 6 months later with an 85% finished product. I refinanced out of the hard money loan into an FHA loan. I had about $40,000 in equity. My payment was $740 a month including taxes, and insurance. I rented 2 spare rooms (found people on craigslist who turned out to be normal thank goodness) out for $450 and $550. After paying utilities, I was getting paid to live in my own home!

Then, a few months later, still not knowing what I was doing, I made an offer to buy a 2-unit apartment house for $24,000 that needed no repairs, seller was essentially desperate for cash. I still didn't really have any money. I made the offer and figured that I would simply find the money somewhere. I went under contract, and then pulled a HELOC from my primary for $10,000 and used that as the downpayment, and got a conventional loan. My payment was, and still is, $234/month taxes and insurance included (15-year mortgage). I rented the top floor (4/2.5) for $550/month. The basement efficiency was rented for $300. I was clearing almost $500 per month. I still own that property, and the same tenants are there, except I let them have the basement when the other person moved out. They don't bother me and the home is 50% paid off at this point.

Then I pulled another HELOC on my primary and bought 2 more.. and then 2 more.. and then I became a Realtor and have since sold over 500 homes, and the rest they say is history.