But I know I won't be able to do my job forever and I like the security and freedom that Real Estate Investing has to offer.I'm currently managing one property part-time but I'm looking to own and manage future properties; most likely out of state.

I also recommend:- the property management book from Brandon - so that you can learn about managing your future property and what to expect- a book on rental regulation on your state.

I’m trying to find a manager who also has knowledge of the surrounding areas, including Houston, Katy, Pearland etc for future properties.

The sacrifices you make today can have a magnificent impact on your future.

In my experience, most agents aren't going to be helpful here (some exceptions).You can ballpark these things after getting some data:Rent:  use the sites  you think you're future tenant will use to find you as a landlord (Zillow, Rent.com, a big property manager in your area, Craigslist) and look for similar places in similar neighborhoods. 

In considering my next move, I'd like to know what experienced investors think about the scale-ability, sustainability, and future of vacation rentals are!

It doesn't really matter for the re-fi, but found it rather annoying and worrying if we need to 1031 this building in the future.

I think I'll try to get my start a different way, but good information for the future.

I have friends from school who had it much better than he did and have completely blown their futures by this point (we are all in our young 30's).

Since I'll be paying cash for properties in the exchange, I'll have a decent amount of equity I can pull out for future investing.