When I started investing, I struggled most with...

[Owen Dashner]

Starting out it in real estate can be overwhelming. What was the thing you struggled with most and how did you overcome it? My biggest hurdle was not knowing when I had a good deal because I struggled with understanding house values and rehab costs.  I overcame it by looking at A LOT of houses.  I would look at a ton of properties online, then call the listing agents on the ones I thought would be decent deals for investors and ask them to show me the listed house.  Then I would get to know them and ask them to send me any investor deals they got.  Going on these showing appointments was invaluable both for looking at the houses and starting relationships with agents who sold "fixer" type properties.  Once I had been through enough houses at certain price points, I started to know what a $100K house felt/looked like vs. a $150K house.

For estimating rehab costs, I spent a lot of time in home improvement stores learning costs of commonly used materials (paint, doors, trim, flooring, windows).  I also made friends with several contractors, so I would always bug them for rough ideas on how much labor costs would be for common remodeling projects.  This helped a lot. 

Granted, I still get rehab estimates wrong all the time even after 15 years, but hey, you gotta start somewhere.

[James De Stefano]

Great points!   As someone who's been in over 100 houses, some flooded, some looking like war zones, some 1/2 way remodeled, and some fully fixed up, it gives you a good sense of the full scope of work needed. 

Good advice and it's a good step towards getting the ball rolling.   Getting your money/ lenders and contractors lined up is another adventures, but none of it works if you pay too much or buy wrong.