At this price point, would a cost segregation study even make sense to do on a condo so that I could take advantage of accelerated depreciation? 

The primary reason why we don't believe the course is worth the cost is because you only have access to the private FB group for 90 days.

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...

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. 

Yes, there is a plethora of leases floating around the internet, but if you want to manage your property properly, it requires a lease agreement that fits the way you want to do business and helps you to cover costs, avoid liabilities, and increase revenue. 

to be direct: your first property, and possibly first several properties, are likely going to cost you money. 

My realtor recommended I get a home warranty to protect against issues that could cost me $1000s of dollars.

I have a series LLC for my rental properties in Utah, but I am not sure how effective it would be for holding a property out of state.2 - I do subject to deals in Utah using a General Warranty deed.

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?