If you have the money to purchase the 4 unit, I would recommend going that route for your first investment because if one tenant moves out you won't fell the "pain" as much as if a single tenant condo were to go vacant.It's a great idea to have an expert walk through the property with you on anytime of investment  but if you cannot get a contractor before you make the offer most likely you will still have some time during you feasibility period to get that done.

Feel your pain.

I've attached one link.From a lender's perspective, it's much more of a pain to do the parent and then children LLC's because we need the entity documents for all of themmost lenders require the LLC to be specific to their transactionyou'll need to keep the funds separated and many times, the LLC doesn't have the assets for reservesthe filing fees for each entity can become onerous and if the property is in a different state, you'll need to provide the foreign entity registration as well as the certificate of good standing in each state   Instead of setting up all of these different LLC's etc..., until you get to a point where you can no longer use Fannie Mae and Freddie Mac financing, get a good umbrella liability policy so you can enjoy the more favorable financing.https://www.biggerpockets.com/renewsblog/the-tradi...

I plan on holding for rental income after purchasing the next duplex.I really do need to get better on crunching numbers so i can figure out specifics myself its just painful to learn the hard-way!

It was painful for me. 

Here are some thoughts:Is the upstairs tenant a pain with other things?

It was a pain in the ***. 

However for truly passive long term wealth I feel that searching out those path of progress properties  and either paying cash for them or financing them can lead the sharp investor to massive wealth and returns without ANY other involvement other than stroking a check annually for tax's and maybe hiring a farmer to keep the grass mowed..example is one I close yesterday  37 acres the family bought 27 years ago for 199k  .. we closed on it yesterday for 7.2 million cash to them.. they did not even 1031  just going to pay the tax and call it a day.. now I don't know if 199k invested in say a few rental houses over 20 or 30 year run would equate to an exit like this.. but for this family it cant get any more passive.  

Gotta be a few that are more of a pain than others? 

@Jeremy Sharp, it's actually super easy.