I live in Bend. We moved here a little over 3 years ago and I love it. It is a great place to raise a family and there is ALWAYS something to do (and typically very cheap or free). If you can secure housing and employment (or work remotely/retire here) it is an excellent place to be. Housing has really taken off here and the rental market is EXTREMELY tight, less than 1% vacancy. Rents have gone up 100's of dollars between lease renewals for a lot of people recently (we don't do this to existing renters, but as an example we have a rental house very close to Drake Park and when our renter moved out because he bought a place, we listed it for $325 more per month and rented it out immediately, like I was overwhelmed with applications after 1 day on craigslist). That said, there is quite a bit of housing that's still affordable but in less desirable areas of town (read: NOT the west side) plus our utility bills are incredibly cheap (at least compared to where we were in TX) as the weather is what I would consider ideal and it's easy to go more than 3/4 of the the year without using a/c or heat. We were lucky and bought in 2012 before things really took off and we have 2 houses, plus part of our main house that we rent out as well.
Fun mustachian things to do in Bend with a baby include (but are not limited to) Juniper Park Swimming Pool, $6 a piece for out of district folks and the baby is likely free, there's a splash pad, some slides etc.
Hiking with the baby in a backpack (our preferred weekend activity). Deschutes River Trail is great and easy with kids.
You can float the river through the old mill and downtown with either your own float or rentals I'm not sure of the price but no more than $5-10 a piece, probably. A local place usually has rentals available River Bend Park.
Sunday afternoons have free summer concerts at Les Schwab Amphitheater at 2 pm. Bring a blanket and food/booze in a cooler if you like.
Our favorite outdoor kid parks are Columbia Park and Harmon Park, both overlook the river.
High Desert Museum is good for a little bit older kids.
Good luck!