Because the chances of successfully concluding a wholesale transaction when you lack experience, knowledge and capital are so infinitesimally small that you’d be better off playing the lottery.  

I do not have the capital for the property to pitch in, so I plan to use the investors money to secure the property.The interest rate that I will pay the investor is 5% for up to a duration of 20 years.

If I was to trade a $300k house for a $310k house that will cost me $10k and $347/month what amount should I ask for to make up for these losses?

I still think if I would have worked it out with them rather than jumping straight to court, I would have taken a smaller loss.

I have a pretty large emergency fund in place for those properties, but I wonder if that capital could be better employed elsewhere (potentially acquire another property).  

You are investing for return on capital. 

I believe in this so strongly that I have even once confronted a large advertising client about this issue when I discovered they had language to this effect in their terms of use in the past, and asked them to change their policy, at risk of material revenue loss to our company.

You’d be able to pull out $330,455, which is significantly more than your initial $236,930 investment.Your Initial Investment Back: This means that in 5 years, you’ll not only get your original investment back but also keep an additional $93k in your pocket.However, there’s a downside:Negative Cash Flow Impact: Over the next 5 years, due to the negative cash flow of $1,229 per month, your total cumulative loss will be $(60,153).

You probably won’t be able to sell with 9 years without taking a loss.

You want an investment that pays for itself, including mortgage, taxes, insurance, maintenance, and even some money set aside for a reserve to cover vacancies and capital expenditures.