Transitioning from normal conversation to a proposition

Hi. I do reasonably well, no problem getting dates. I'm also pretty good at flirty, challenging and provocative texting/messaging. How they respond to that is their thing, I don't fear any rejection there. I'm a writer, and I've absorbed enough game theory to pull this off easily. And flirty messaging sets up the intention in the girls mind before the date. I present well on dates, I'm funny, I'm a nice and genuine guy.

Problem is, once I'm on the date, I'm actually too nice. I have difficulty transitioning from normal conversation to a proposition to come home with me. Or steering the conversation into direct flirtation or how to gauge her actual willingness for a ONS. I can text flirt well, but in person I get shy about following through with my intentions. Most of my dates end with a hug.

In the past, I have used the first date as a soft opening, then with texting I follow up a day or two later with some direct proposition, to see if she's interested in fast forwarding. This can take time and has more places to abort. Again, it's this fear of making my move in person, on the spot.

It makes me really nervous to do this. I always feel like zeroing in too abruptly is off-putting, and a direct proposition is too forward. I'm too nice. And it goes back to my high school years, just being too nice and passive about things. I was never assertive with girls, until learning some game in recent years. I don't want to objectify the girl or be seen as objectifying her.

I often notice when conversation goes in this direction, a girls wall goes up because they don't want to be perceived as too easy, or being objectified just for sex.

I know this is just my biased mentality and I'm wrong, but can anyone offer some tips on strategic thinking to get past this? Or even dialog? How to steer things towards a proposition.

Another problem is that I live in a small town about 40 minutes from a big city. There is not much of a dating market here, so I often go on dates in the big city. And asking a girl home means asking her to follow me in her car for 40 minutes, which just seems to kill the spontaneity and becomes like, work. It's logistically difficult. Any tips on that too.

Thanks!