The other option is to rent but to hire someone to manage your rentals.

Should I maybe suggest he try syndication or even a lease-to-own option? 

It is possible to do the FHA loan in FL since it would meet the distance criteria, the DTI on existing property would be a possibility but there is always options that do not unfold until all the information is gathered. 

I would think the best option for you is to try to get around as many likeminded people as you can and be active on these forums.

I am exploring two options as a new investor.

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Kind of in a pinch for some capital, and the only other option I’m considering is a straight cash out refi to avoid the risk.

-Setting Criteria: Defining specific criteria such as location, property type, Financing Options (Including Seller financing), and comfort level to narrow down options.a.

I currently have properties in my name but starting to scale so looking at different options.

Here's what I decided to do: I explained the situation to my new tenant and asked which option was better for her; self-install it for me, or have me send someone to do it.