Do lawn-care/snow removal myself or hire out?

[Michael Doherty]

Hi all- looking for opinions on whether or not I should hire out for lawn care and snow removal on my properties or buy a truck and do it myself... let me explain my situation. 

I currently do not own a truck but would really like a beater truck to have for random things and project ect... As of right now, I own 2 Multi-Family properties and my gf is closing on another (3 total). Our plan is to keep acquiring more and build a portfolio. 

I keep going back and forth on whether or not I should mow and do the snow removal on all 3 properties or hire out. Albeit, 2 of the properties are within 5 miles of each of each other and the 3rd is 25 mins away. None of them have extensively big yards or driveways and realistically would take 20 mins to mow and less to plow.

Couple things to think about: I currently work 40 hours a week.... would you really want to spend your weekends and week nights taking care of this? Opportunity cost of looking at other deals/ enjoying life. You Could write off the landscaping/snow removal. In my area the cost of mowing every other week would be roughly 50-60 bucks per month per house. Snow removal is anywhere from 35-50 a driveway. I live in New England so there could be snow twice a week or once a month. Can you really justify paying someone to do the work when you live close, are you just being lazy?

Lastly and thank you for bearing with me, I have plans on purchasing a truck regardless..... so it's not whether or not to buy a truck or not... it's at what point do you hire out and build a good system/network or take care of yourself?