As in most of these cases, it can work, but rarely does, needing a unique set of circumstances, and a unique, possibly extra motivated seller.  

Niche: Buy & HoldStrategy: House-hack 1st investment Challenge: Expensive area (Bay Area)I want to start my real estate investment by using the house-hack strategy for the first investment.

Pick a niche and educate yourself and dive right inI started part time and am transitioning full time.  

I've just gotten into real estate investing am am just trying to find my niche and after listening to the podcast, I think it might be wholesaling.

So many unique places to go.  

@Eric EspinosaWelcome to the vibrant BP community, where you will find like minded individuals committed to REI and also helping others succeed.Your time on this social media site will be well spent.You have taken the 1st step by announcing your readiness and commitment to embark on a REI career.I didn't see any mention of your particular REI area of interest, but, whether you pursue, wholesale, rehab & fIip or buy and hold it's up to you to decide.I added three links below from the most popular niches for you to pick one, focus on it and expand to the others if needed later.https://www.biggerpockets.com/renewsblog/2015/01/31/ultimate-beginners-guide-real-estate-wholesaling-2/ (Ultimate beginners guide to wholesaling)http://www.biggerpockets.com/renewsblog/2014/01/07/flipping-houses/ (step by step guide to flips)http://www.biggerpockets.com/renewsblog/2013/02/22/buying-rental-property/ (how to buy a rental property)Also, in reading your introduction my take is that you should stop thinking of the past in terms of could have, would have and should have.

Those who lose in the market are not diversified in their knowledge, being stuck in one niche or another can be a short life span in business.

Learn as much as possible, develop some great contacts, determine what your niche will be (style of investing), set some goals, and continuously improve your financial situation.

My marketing goal (stay tuned for 2 new, unique marketing websites), will focus on attracting the home farming market by creating strong relationships with organizations like Future Farmers of America (and others), to assist younger generation, new American farmers matched with land at affordable prices and with easy lease-purchase options.  

For starters, I would try to determine what your investing niche will be.