So many intellegent and supportive individuals on here, you will get out what you put in.

I’ve been in the real estate business as a broker, helping clients buy and sell homes, but I’m looking to take things to the next level by diving deeper into investing.

I was wondering how people managed to scale their businesses faster.

Are in any business affiliation with Dustin Ruhl? 

Sights are set on all types of REI, but this will be a great start for us.I have been in the mortgage business for over 20 years.

Looking to either sell individually or as a package to an investor.

Although most of my stays are <7 days, I've had a few longer stays (business travelers and a family that was going through a full home remodel).

I've actually pulled the plug on investing to focus on our general contracting business because investing was more of a distraction.  

Quote from @Gregory Wilson: A few things there, Brendan.First, an LLC with you as a member and your (wife, son, pal, etc.) partner as a 1% member will file a Form 1065 which is about one tenth as likely to be audited by the IRS as a Form 1040 with a Schedule E rental activity (which I presume you will attempt to show is an active business).Second, you want an LLC because when your local Alabama handyman drives his girlfriend's uninsured truck into a van load of U of A medical school interns on I-22 when he goes  to get some shingles for your roof, on your business, you don't lose everything you have or ever will have to an uninsured claim. 

I would focus on being an agent and building that business.