For me my biggest hurdle is just finding the right deal and going up against investors with more money than me. I'm thinking its because i'm in California.
After paying off over 100k of debt I finally was able to save up 40k to start shopping for a home. I started looking at houses for my primary residence about 4 months back. I was mainly looking for fixers due to myself having some construction back ground I wanted to fix up my own home. However, when ever I saw what looked like a good deail, (only 80% of market) i'd contact my agent and schedule a walk through. Since I work full time I only have time on weekends. But many times by the time the weekend rolls around the house would be either pending status or backup offer status.
After a few weeks of this I decided on a change of strategy. I would look for houses needing less TLC. But those houses in the area I want are 475k+. I would have won a bid for a house at 490k but after losing a whole nights sleep thinking about a 3k monthly mortgage I decided it wasnt for me.
I just dont konw how people do it in LA. Which now has forced me into another mind shift. I"m now contemplating whether or not to buy a condo and after a year buy a 2nd and renting 1st out. and keep doing that for the next 3 years. but that strategy would only allow me to buy 3 condos in the next 3 years cuz my debt to income probably wont let me buy 4th. And after the 3rd I'd probably be stuck for awhile until i can save up a lot of money.
Or an alternative to buying condos in LA would be to invest out of state. But so many unknowns and so scary when the investment is so far away.
oh boy! didnt realize it's been such a long 4 months. Sorry for the lengthy post.