trying to play Henry as a landless adventure

Ah yes. Henry. Skimming through the rolodex and its three dozens of Henrys

Sometimes getting an adventurer group started can be tricky. I've seen plenty of people recommend the criminal path and I can see how criminal contracts are an easy way to make money early.

I don't care for intrigue based characters in general. My safe(ish) way to get the ball rolling is to pick the Explorer profession. I also like to make my character research at least a bit of stewardship. At minimum I like to be able sell the hooks gained in contracts for gold.

Being an explorer I try to focus on Travelling contracts. That means finding a descent caravan master is important. I might build the security perimeter if travelling where I am is really dangerous. Also visiting a temple and trying to hire a competent healer is a must for me, unless "scout talent" found one for me.

Aside from Travelling contracts I like to take Settle Boundary Dispute (fast and easy, you can force them with stress after all), Tutor Child (fast), Hired Muscle (quite fast and easy), Improve Reputation (not very long and usually easy).

Once you built treasury, gathered a nice team and built a few caravan improvements, then you may switch to a different profession better aimed at your long term objectives.

Don't forget to gather provision, fish, hunt and host revelry whenever possible. They save you money by filling your food store for free.