Unfortunately my designation and degree don't mean much when it comes to doing your own electrical, or drafting your own plans.I have a three family home, I plan to gut reno three bathrooms, and kitchens, and the building department wants stamped plans since its a 3+ unit.

The way to get started is to educate yourself on the business, the market and the costs associated with the business at all levels from marketing, acquisition, closing, rehab, carrying costs, closing etc.

I would also recommend you look into the BiggerPockets bookstore, which can be found here: https://www.biggerpockets.com/storeI'd also recommend you join the Pittsburgh Real Estate Investors Association (REIA); simply Google "Pittsburgh REIA," and it's the first link.

You'd have to deal with payroll and associated payroll taxes. 

To do this I think he should attend college and then use that degree to save money, learn the business, network and obtain a RE license.

If they type it up on a standard state Realtor® Association form you will probably be fine, but still read through it carefully.

I am currently attending the University of Missouri, but I plan to work and reside in Kansas City following the completion of my degree.

Now that I've learned a bunch from the site my next deals will be better.My advice to you - get a good job leveraging your degree once you graduate and max out that W2 income while you continue to learn real estate. 

An associate of mine was using Buildium for a couple of years and she had an accounting mess but I think it had more to do with her than the software, I switched her over to Appfolio and now do backoffice work for her and she's happy.But like Nathan said, take advantage of the free trials, pick one and run with it, they are all good it just comes down to personal preference in a lot of

Local REIA is called Freedom First Real Estate Investors Association.