I think it depends on the person honestly. It gets old/boring if you do it way too much. There were periods were I would 3-4 times a week, and that was overkill. It got exhausting arranging something and then having one flake because they were busy/tired/too high/whatever their issue. You would have to repeat it several times with different ones, then go to their location, it just takes a lot of time. But you know you will get laid once you get there. I'd say 1 to 2 times per week makes it exciting and keeps the rush flowing.

I do crave certain women sometimes but am open to any. I have had as young as 18 and as old as 62, all ethnicities basically, various sizes. Each have something different to offer and I think variety is good to try out if you are just starting out.

Most of my encounters are paid, I do get laid for free too. Getting laid for free requires a lot more work but the sex is a lot more rewarding. I am part of a few swinger sites and the swinger community. I get laid 1-2 times a month like that and, to me, it is the most enjoyable sex. The chick wants you, it is just raw passion, and lots of fun. Don't assume you will get laid the next day though. I have been doing this for years and only get 1-2 sessions a month like that. The women aren't necessarily young and hot either, so keep that in mind.

You don't have to be an asshole to get laid. Just put yourself out there in the swinger community and hangout where older women tend to hang out if you are a younger dude. I used to cold approach older women all the time. As long as you are decently fit and average looking, you are going to find one that will fuck you. That confidence will help you find more. I think cold approaching older women is really something that younger guys leave out and miss out on.

Pay if you want to have something quick and get over with it. Her hotness will range with the $ amount you are willing to put up. Do some cold approach with older women and join the right swinger communities if you want some free action. Don't expect a hot girl, but you will get your dick wet if you put effort there.