Without taking too much of your time, let's jump right in.Rent comparables, using the lower-mid end of the market:1/1 - $14753/2 - $2500Mortgage 30YF @ 4.359%, 14% downTriplex- 3/2 & 1/1 & 1/1Asking Price 519,000EGI65,400 - vacancy (5%) = 62,130Yearly Operating ExpensesTaxes (1.15%) - 7,785insurance - 1500 repairs (5%)- 3270CapEx (10%) - 6540PM (10%) - 6540Utilities - 1500Total Expenses- 27,135NOI= 34,99534,995 - 27,384 (mortgage- refer above) = 7,611$$$634$$$ CASH FLOW per month, or over $200 per door for this multi in LOS ANGELES, CALIFORNIA CA!!

(get data points to compare)Is it in a good area with reasonable chances for long term appreciation....?

Watch the properties see what they sell for and compare your numbers. 

I'm thinking if they keep paying reliably, up their rent by $50 at renewal time and then they'll either stay or decide to self vacate?

That just doesn't feel right to me :) So, if you want to hire somebody to buy and deliver stuff to vending machines you need at least 10 machines, because otherwise the salary of a person would be too high compare to profits you are getting from the sales.

Been looking for a few weeks now for some consistent and reliable wholesalers in SoCal, mostly in the Inland Empire area, to pick up some deals from. 

Tell the attendees you will keep them notified by email list or Meetup notices, which ever you choose, and then either collect those emails, or ask them to join your group on meetup (emails are more reliable).But make no mistake, running a group is work, even if you keep it simple. 

For the area it's in the rent is low compared to what I could be getting (some homes in the $1000 to $1150  range).  

Do your research, start with rentometer.com then check local listings, make sure to compare apples to apples.

If this contractor is known as being reliable, or was referred to you by a reliable source, then you've already taken a load off your shoulders.