How do you know whether to avoid a person or not when traveling?

Pretty much the title. I travel full time but when I see folks out on the road who look like they might be in this community, flying a sign or chillin at a gas station, I pretty much never strike up a conversation.

Two reasons:

1 - I feel like I’m bad at reading people/situations

2 - I feel like a poser and like I won’t be well received. I’m a rubber tramp and I waited till I was in my 40’s and had a bit of cash behind me before I quit the bullshit career and started wandering.

Any advice? I’d like to be a little more bold and share conversation and a drink or a meal with some of you real ones out there. Maybe do a little something to share with some who haven’t been as fortunate as me. I worry I’ll be taken for a sucker, or worse though.

I’m coming from a good place so please don’t tear me apart in the comments.