"Adding a lawyer to your team" is good general advice, but awkward in practice. 

No one likes awkward conversations, most people will go above and beyond the money to avoid them.

I'd love to hear about your experiences when you've attended a meet-up and felt grateful and excited that you had braved the highly awkward first 20 minutes to stick it out and gain a positive result. 

Might be awkward for the friend in the middle going forward. 

We purchased it as a very awkward single family home and converted it to a legal duplex.

It's just awkward and tedious for a manager or owner to do bunch of small tasks.  

At the end you will have much more work to do, finding 2 tenants every year and again dealing with vacancies.4) Timing - if you rent to students in collages make sure your lease is not timed awkwardly.

We are caught up between having a practical flowing kitchen, with a fridge where the dishwasher would go, or a less then desirable flow, with a dishwasher but the fridge in a some what awkward spot.

An awkward layout and motivated seller was to our advantage.

It is awkward, but we are very up front about it.