I did something similar, but I bought the homes cash instead of financing. I bought most properties as short sales and a cash buyer seemed to have an advantage (maybe I was wrong?) so I always offered cash. I always had to put out a few bids at a time since even the most promising bids seemed to have a ~25% success rate.

To buy at least one every year I had to take out a low interest HELOC on the first investment purchase to help finance the new ones. Thankfully I was able to pay the prior HELOC amount back in full prior to buying a new one and just keep using the same credit line since there's a 5-year draw period.

I live and buy here in southern CA so the prices have risen to the point where I don't feel comfortable buying anymore, but thankfully so have the property values of the homes I do own.

I never looked into getting my real estate license, but we have a great agent now who we've bought our last four homes through (including the one we live in). She also recommended an excellent property manager that we now use exclusively (our last one was worthless). A good property manager makes all the difference. I actually spend more time sorting the taxes for the properties than I spend doing anything else for them, and that's one a couple hours a year.

I think real estate is a great industry for hackers. I've always been good with money, but I had no background in real estate when I started. I could have done a lot of things better and I probably got lucky, but it's still a goo industry for us.

Investing in equities is too information-centric and it's hard to compete or gain a legal competitive advantage. But in real estate the market is so fragmented, varies by region, and realtors are so old-fashioned that it's easy to gain an advantage if you think differently.

I suspect that anyone who can run a startup as a single founder (i.e. they have a wide range of skills) could dominate the real estate market in most non-major cities within five years if they wanted to. If they document and systematize their process, realtors would pay tens of thousands for it a pop. Real estate agents tend to always be looking for shortcuts, are unfazed by loud and spammy advertisements, and want new quick ways to get leads than most other markets and have a lot of money to spend doing it, especially here in southern California where a commission can be over $100,000.

If I weren't set on running my company for the next 10+ years I'd probably go into real estate to see if I could do what I suggested above. Anyway, a few closing tips: find a good lender if you borrow, find a reliable and reputable inspector before you decide, thoroughly research the area (historical prices, industry, jobs, schools, crime, future major builds plans, etc.), and condos are easier to manage than single family homes since the HOA covers everything, plus your margins are higher.