@Dustin Horner you should be contracting maintenance work and creating a preferred list of vendors as @Phillip Austin has recommended.The first person you hire to help you should be to handle what you LEAST like to do yourself or has the greatest time savings for you!

I don't have personal experience with it, but when the app was first developed, I contacted the developer and put the app through a fairly robust test usage to see if it's something I would want to recommend to my clients (I'm a CPA).I think the app is great for its intended purpose and I do recommend it to my clients now (and have for about 18 months now). 

And personally, I stay away from OH because it's what herd think has long been and I worry how much of price is based on herd-actions or market metrics. 

Can this person now be "a real estate" professional? 

Personally, I've been in this niche since 2007.

The terms and costs will depend on the property, your personal situation, the location, etc.

Quote from @Mathew Chacko: Quote from @Na Person:  I too was a little skeptical of sending a large cash payment to an unlicensed entity (1031 facilitators do not need a license). 

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I personally don't like getting a lot of automated messages when I rent a STR, I'd rather have some more personal contact.....

I would recommend targeting 30 day minimum rentals (Most associations are 90+), allowing 12+ rentals per year (most allow 1-3), and no in-person screening for tenants required.