As part of his investment of capital into scaling, he hired a marketing firm specializing in SEO, SEM, social media, direct email, etc.  

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.

You are investing for return on capital. 

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 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).  

that may work for others, but i don't have enough capital to do that, and the returns are in the tougher strategies (like STR - i didn't look at your other posts, but if you are successful in STR, that's great.) 

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 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.

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.