I'm trying to get into the market rather than sit on the sidelines, but my biggest fear is getting trapped in a big mortgage only to watch the value of my home fall. 

If we all feared slander over warning other people, then we would enable Scott to continue this behavior. 

I have to stop putting artificial limits and stop fearing failure.

Today, the one deal I was working where fear got in my way is really what I want to talk about. 

To me, buying the first property was always the hardest, mainly because 1) I didn't know what to expect and how to deal with the pains that come along with being a property owner/landlord, and 2) fear of failure (completely losing my investment). 

@Cody L. indicated two $100K properties and I understand his rationale but I fear $100K still leaves you in a poor class area and so using similar rationale I would recommend a single financed $200K RE that is in at least C+ class (and preferably B class) area or do as @Brandon Burns suggested and partner.If you purchase a $50K RE OOS it will be in a poor area that has historically zero appreciation. 

Maybe they didn't know, but they should be putting pressure on the seller to release the money.I fear the inspection and appraisal money is lost.

But I was telling my wife that don't fear loosing out on the time and money investment all that much.

So, if they are incredibly rare (which I fear they might be) once you've used your four or five (or ten) loans... how do you keep going? 

What I like are 1) Potential: up and coming neighborhoods/city development 2) Weather 3) Scenery 4) low cost of living 5) It's my wife's idea (for real this time)It seems that you live there, as well as, @Greg Seawell (thank you so much for your reply and willingness to help), I'd really appreciate if you could give me a realistic sense of how true/false my fears are.