I realize I'm a bit late to the party, but I'll still give my two cents for anyone checking this down the road. I was new to the world of bikes when I bought my first one exactly 8 years ago. I was 39 years old when I sat on my first motorcycle (my wife's only requirement was that I have life insurance, so when I die she will be a wealthy woman). Thankfully, I had a life-long veteran biker (65-70 years old) that helped me find one and get it running. My first purchase was an '87 Yamaha Virago 700. Nothing pretty necessarily, but it was perfect for my build, inexperience, and season of life. I am 5'9", 180 lbs., and am fit enough to handle things when I need to. I cannot tell you how beneficial that bike was to me as a newbie. As a cruiser, it was low to the ground with a great center of gravity, and had enough weight to it that the 700 engine wouldn't buck me off if I got too throttle happy. That was the only bike I knew for the first 6 years.
From there it was an '87 Suzuki Cavalcade 1400 (their short-lived touring bike). It was a big step up, but if I hadn't had the road miles in my portfolio from the past 6 years it would have been very dangerous for me. From there I bought an '07 Nomad 1600 with less than 3,500 miles on it (you read that right --- less than 3,500 miles after 14 years from just one owner. BTW I only paid $3500 for it! It was an amazing find). I love this Nomad. I love the sound. I love the look. I love the feel. I love most everything about it. The only thing I don't like is the seat, which I am having replaced with a custom seat this spring which will be wider, softer, and with more support. Though this bike handles great, I would not have been able to manage it as a new rider. Even with my experience now, there are times (especially when coming to a slow stop at a light) when I find myself having to really focus on not tipping too much. It's just that much heavier than a 700-900 size bike. I never crashed my 700, but I did drop a couple times. I did not cry at all because it wasn't a real looker like this Nomad is.
My final assessment: buy small and cheap, and buy up when you are ready. I don't regret working my way up to this bike, and it is that much more rewarding for me now that I have enough experience to really enjoy the ride. And as a side note, I also have a 2018 Yamaha V-star 250 that I bought for running around town (can't beat the mpg) and for teaching my kids how to ride. It's almost as light as a bicycle and I picked it up as a 3-year-old bike with only 12 miles on it for only $2000. Again, a great find. Be patient and buy a bike that suits your age, size and experience. You won't regret it.