Picking up MILFs from Target

Sourcing

Hit up organic supermarkets (wholefoods/local owned co-op) and local coffee shops, target organic and specialty. Also go for fitness classes (think pilates/yoga/spin) for this strat you have to fight off the perception of being a creep and being gay, if you have to choose then play into the second one - best advice I can give is to just act/be genuinely interested in the class, get there early, put in face time and build rapport with instructors, you will have the MILFs gravitating to you.

To practice your approach consider college campuses on tour days or move in days. Lower rate of success, however high frequency means you can use these to perfect your pitch and story. Added bonus is you get to hit on MILFs in front of their kids.

Identification Strategy

Identifying MILFs is difficult, you can go for ones still married (high-risk, high-reward) or divorced MILFs (safer bet but don't get greedy and stay too long after the pump and dump - you'll end up with a liability).

Now the obvious play is to check whether they have a ring, but this doesn't mean anything as a standalone data point. If you see the same MILFs regularly, the key is the variations in ring wearing. If Jenny from yoga always wears her ring and as she is talking to Lauren about being stressed you notice she isn't wearing it, this is the time to work on your distressed buyout pitch.

My go to play for identifying divorced MILFs is look for their assets showing their age (if they have a higher end car (Cayenne, lexus SUV) but it is 5+ years old, potentially they got the car in the divorce but don't have cash flow to trade in).

Building Rapport and Winning the Engagement

Here we get to the pointy end. MILFs aren't your startup CEO that has their eyes set on an IPO, as such, they require more pitching to close the deal.

Here's a scenario - MILF with no ring, in wholefoods, dressed in active wear

The strat here is to check the trolley before you approach, this can give you vital info that means you can personalize your pitch. Think: how many people is she shopping for, is there any pet food in the trolley, check for dietary trends (vegan, vego, etc), and does it look like she is buying for kids/teenagers.

One strat for approaching is the faux question turn compliment maneuver; "Hey, that (dog food/vegan something/niche snack) looks grea- oh wow, you're beautiful". From there, introduce yourself, shake hands, and start asking about them (name, vegan, yoga, etc). Note on compliments is do not be overly sexual, this isn't MILF specific. 

Note

Despite being harder to break into, MILFs are lower cost and less demanding work than models and bottles, however there are less perks (think head while driving). Good luck OP.