Like most new investors starting out, I have a few good things going for me (steady income, great credit, education resources, support from family), and a few barriers to overcome (no cash, no assets, limited network).

Some questions I have about the process.What hurdles do I need to overcome when adding a living structure? 

This helped me TREMENDOUSLY overcome my personal analysis paralysis. 

Now if you have illegal plumbing and other things, it might get messier.The basement is likely not going to fly, as there are usually structural issues with egress and natural light that might be difficult to overcome.  

That's a shame but I'll overcome and adapt!

If you give the seller a unrealistic expectation you will need to overcome that later or lose the deal!

What do you think was the toughest obstacle to overcome in that short sale purchase or what as it that you didn't think to be as difficult as it turned out to be?

If so, how did you overcome the situation without damaging the relationship with them?

I hope that these are two hurdles that we will be able to find creative ways to overcome.  

And sometimes the long hold time can result in appreciation that overcomes bad execution...something that is less likely with flips (but is a driving force behind the many posts you see that say "we meant to flip it but it didn't sell so we decided to rent it out"...whoops).One way to balance the risks in flipping is to do it in a fund structure, which gives diversification amongst several deals at a time so that one blown deal is a drag on the overall vehicle but doesn't wipe out an investment.