How many brokerages did you meet with before making a decision, and what were the key determining factors that influenced your decision?

I had a discussion with a colleague about a tenant who damaged their apartment.

One exposure can damage your lungs permanently.

If the previous landlord did not do a good job of documenting the move in checklist there is no way to determine ANY damage the tenant has caused. 

That includes towel & linen rental, off site laundry and basic consumables.AirBnB also lumps in the Limited Damage Waiver ($59) and Hotel Occupancy Tax (5%) and AirBnB listing fee (3%) to the total "cleaning" cost paid by guests.175 + 59 = 234 x .05 = 245.70 x .03 = 253.07 (Rounded to $255)The good news for you - These are all expenses that must be paid.

The other thing is you're buying very low end properties which will attract low end renters which will be more likely to damage your property and just not treat it well.

He pays me market rent and is responsible for any damage caused by his tenants and also minor maintenance. 

Good tips on doing this and keep from ticking them off to the point they’ll do damage?

I'd avoid them because if the tenant damages something, you are going to be on the hook for repairs.

So here are pros and cons of managing yourself.Pros:  you keep all profits (except 3% to credit card company), get to know guests, create a rapport with regular guests, make it personalized and memorable for your guests (my housekeeping staff was great and would leave flowers for anniversaries and balloons for bdays)Cons: Phone calls late at night sometimes, dealing with guests who are nasty and ignore your rules (ie no pets/no smoking, but it's nice having damage waiver in place), trial and error finding right housekeeping/maintenance/HVAC/plumbing people.Going with a property management company pros and cons:Pros:  they deal with all the issues and reservations callsCons: they may not be as attentive to your property as you would be and don't follow through with rules of no pets/no smoking.