TwoSheets, I went through this exact same process 9 years ago. T/S or keelboat, power or sail, moored or berthed. In the end it came down to how easy it was to go sailing. Plus, I only had $10k. So that limited me even further.
Plus, I don't live too far from either Sydney harbour or Pittwater/Broken Bay, so towing wasn't a biggie. Rigging was, as was storage and wash down after a day out.
We've now had our $10k Top Hat 25 for 9 years. Over that time she's been up and down the local coast a few times, but mostly weekends and day sails in Pittwater/Broken Bay and Brisbane water. We still haven't seen all of it. She gets anti-fouled once every 18 months, regular checks on the rig and most of the standing and running rigging has been gradually replaced. Mooring and Rego fees are pretty reasonable and I'd estimate over 9 years she's cost a total of $30k - $35k to buy, keep and maintain. Sure, she's not the prettiest boat in the bay, but she's easy to sail single handed, can handle a blow and Top Hats have been around the world and around Australia many times.
It takes 30 minutes to drive to Careel Bay. 10 minutes to row out, 10 minutes to open the boat and get her ready to go. It takes 10 minutes to pack her down, put up the nets and 10 minutes to row back to shore. 30 minutes back home. The only other thing I do is load and unload a rooftop dinghy.
If I had to drive to the bay, rig a mast and launch, I'd probably go less than the twice a month I've averaged recently. So consider how often you want to go, who you want to take and what you can get for your money these days. Oh, and consider whether you want to race. I don't, and won't ever. Not really my thing.
Enjoy the research though and don't be put off by the naysayers. Either way, a keelboat or trailer sailer, the view when you're sitting at anchor at sunset will be exactly the same as the bloke on the multi-million dollar gin palace