Property Management Business Plan

[Travis T.]

I'm hoping to get some feedback on an idea I've been kicking around for some time.  I'm not a business major...

I'm nearing the end of one career, and will be transitioning in the next two years to a slightly different field.  I currently have one rental home in addition to my primary residence.  My long-term goal is to build a rental property portfolio that would provide enough passive income to live comfortably.

I am currently managing the one rental property myself, and want to continue to manage it and any other properties I purchase as a "part-time" job.  Included in the "management" of these properties is a good deal of skilled labor jobs (repairs, renovations, upkeep, etc.).  Eventually, when the cash flow from the rental properties is enough to replace my day job, I'd like to transition to managing my properties as my primary job.

I'm trying to test the waters to see if this makes sense from a business/tax perspective.  I also want to do this right from the get-go, instead of just winging it.  While setting up a company is not absolutely necessary to do maintenance on properties I own, it (along with the proper licensing) allows me to do work on homes I do not own.  While this would not be the primary purpose of the company, but would be an added benefit.

Does this sound reasonable?  Please talk me out of it if there is a reason I should not do this.  I will gladly elaborate on more details if that is helpful, but wanted to keep this first post from being a novel.

- Travis