I think if your tax return is simple(W-2 and a couple of interest/brokerage accounts), then software like turbo tax, H&R block will likely do just fine.However, when you get into investments(Real Estate, Syndications, etc), you may be better off hiring a professional.I think it is a good idea to match your tax profile with that of the professional.If you are a real estate professional, work with a CPA who understands real estate taxation.I also think people need to find the right fit with the CPA.I often find small real estate investors try to work with a large firm where their target market might be large institutional investors.

These can be a real pain. 

It sounds like your friend just needs some additional support around him.......and I feel his pain. 

Bottom line: I feel your pain...

If you're interested in the subject, a great resource for tenant/landlord laws in the LA area is Dennis Block's website.

Once you purchase and renovate a home introduce yourself to the block club and advise them of your intent to make an impact. 

She again states she didn't know she couldn't park there.... same conversation again.Vehicles get moved, but now the RV is blocking our access road.  

As an Interior Designer/Project Manager who’s done Home staging I’ve  had to work with flip houses that lacked forethought and or quality execution for some realtors trying to market that basic “lipstick on a pig” approach and I wish their flip investors had called me from the planning phase…You may not need an Interior Designer to oversee every step of a renovation but what I’ve been asked to stage after poor choices in style, colors and materials it can be painful. 

Florida has been a real pain getting good coverage, that's another topic.

Hey man,I feel your pain, everyone has gone through it.This is what you should know...As you keep doing it, you will start to get better at it.