After a few months of being a landlord, I feel confident in expanding my business to a couple more properties. 

The numbers:Purchase Price: $118.5k Hard Money Rehab: 30kARV: 218kDown payment: 10% of purchase and 10% of rehabTotal Invested funds w/ closing: 24kHolding costs: 1700Hard Money payoff: 134kREFI Option:75% cash out refi of 220k= 165k loan, 30 yr fixed @ 6% and 2ptsPITI: $1500Gross Rental Income: $2600Monthly Cash flow after expenses: 750If I decide to sell I will need to spend 5800 to paint the exterior but based on comps I could confidently sell for 220-230k.

I think confidence, and trusting in yourself is key in this industry.

Shaun,How confident are you of the value of $349K?

The good thing about the property is I lived 5 years mortgage free, so now I have the capital to confidently pursue more (better) investments. 

I want to prepare myself post recovery so I’m confident in my offers and minimized my investment risk

You could also try role playing with a friend to gain some repetition and confidence.

Once I have some experience under my belt to show for then I feel the investors will be more confident in me. 

She told me what the highest offer was at the time ($55,000), so I'm confident that she told the final person that my offer was $57,500... thus the final price of $57,550. 

If your looking to get into rentals and you know the school system isn't the best but the market is flooded with renters, than feel confident that you will do just fine.