As @Chris Mason mentioned, the ability to hold here is extremely important.

become very familiar with DTI and how it works because you need to understand what you are buying now will effect your ability to buy in the future.  

Even if you don't like the way they keep the unit, you will have to give you notice and the ability to clean it up and can't just start an eviction and destroy their ability to find another home.

You mention not having the ability to book online as a negative.

I have the ability to completely wipe this debt but I also do not want to part with all of my capital as it will delay my ability to invest.

I like the idea of having the ability to provide a tenant reference, that is a really good idea.

I see a child in the picture which adds complexity to your ability to do a good job.  

A Broker will have the ability to basically shop many different banks for you.  

I guess I'm just worried that with my travel schedule (I'm on the road a lot for work) that I wouldn't have the time and ability to be there in-person.

I've been kicking around the idea of applying for a HELOC immediately after closing instead of waiting 6 months for a conventional cash-out refinance.I spoke with Wells Fargo and they can do a HELOC up to 80% of the purchase price with no seasoning and I would have the ability to do 80% of the appraised value after 12 months.