Seller is paying $5,000 of closing costs and a $5000 credit towards a contractor for repairs found during inspection.Here is the part that is bothering me...

As far as the cost segregation study goes - yes, you can absolutely do a cost segregation study on a new build.

I am unsure if they are a good investment, but I am leaning towards yes, I don't have anyone around me to ask so I decided to come here.House 1. rents for $825/m the loan will cost me $13,000 as a down payment and $6,000 closing costs, and should cash flow approx $275/m after mortgage payment are made.House 2. rents for $600/m the loan will cost me $13,000 as a down payment and $6,000 closing costs, and should cash flow approx $50/m after mortgage payment are made. 

I am very eager to start taking action and learning but live in a high cost of living market (Boston) currently and for several reasons (need to save more, move to lower cost of living place etc.) will not be able to start for at least 1.5 years. 

How much will it cost to get me the licenses?

If not, do you know someone that can manage it for you and is there enough money available to cover their costs?

You need to get a clear understanding of the cost to repair, if it can even be repaired.

If buyers are financing with 10-20% down and hoping to secure a competitive property, I'll provide them an accurate competitive market analysis (CMA) and have my lender partner (or myself as a licensed NMLS mortgage broker) breakdown the differences in loan terms for an escalated at various price examples. 

Negatives are that there is an additional cost for me and if the tenant doesn't pay the water bill, i would end up with a potentially large bill at some point. 

@Lucas Carl, When you talk about your cabin with a purchase price of $500k, I'm assuming a 25% down payment + any costs to furnish/fix/renovate as the initial cash outlay (for example $150k total).