First investment property

[Wilson Rith]

Hoping this the right forum for this question.  So I am starting out, and these are the two scenarios that are playing out:

1) Three family with renters already but these properties are going for around 400k, almost 150k above there assessment value.  I'd have to live in one of the units.  Is it hard to get one of the renters to leave, so my family could live in an owners unit?  Is this negotiated during buying?

2) Three family units with no renters.  The rental demand in my market is strong but i've never screened for renters before.  These houses needed a little tlc.  There is one in my market that is 289k. Should I take a 203k, make it rent ready (vs my own house ready) and than find renters.  The mortgage at this place would be around 1600, and my wife and I already pay 1325 in our own apartment.  So we could cover rent if the place goes unrented for a while etc., Well if I rehab the place a little bit than the mortgage may be higher.  Mortgage for situation 1 would be around 2,500/mo.  Which would be harder to cover if something happens, but again they already have renters.

What are your thoughts?