When we looked at boats a 1979 Cal 27-2 had a porta potty, a tiller, and an A-4 gas engine.
I'd have to admit that with a porta potty and a gas engine, the boat had no smell whatsoever. We would own that boat if we made up our mind on the spot, but we called two days later to offer the asking price and she was already sold (price had just been reduced so it was no surpise).
Our Starwind had some features which we thought were on the plus side ... diesel inboard, fixed head, and wheel steering. We still love our boat after 7 years but we found that:
1. The diesel engine is noisy and one cylinder shakes like hell, it belches black smoke and soot when it is started, and diesel fuel stinks and it is hard to get rid of the odor from even tiny leaks. The smell and noise of a diesel engine is far more objectionable than a gas engine when they are running. OTOH, complaining about diesel engines to sailors is like swimming against the tide, and you may as well get used to the fact that owning a diesel with your boat is inevitable if you are going to have an inboard engine.
2. The head was poorly maintained by the previous owner and a bad odor permeated the entire cabin and all of the cushions. I ignored that problem when we purchased the boat, thinking that it would easily be fixed. It wasn't. We replaced all the cushions and fabric at significant expense. I replaced the head and the hoses, which was a really nasty job. I would replace the tank if I could get it out without cutting out fiberglass. It has taken a lot of time and effort to get rid of the stink - way more than I anticipated and I would never make that mistake again.
3. Wheel steering in the cockpit of a 27' boat is a marginal upgrade. If I was a regular single-handed sailor, I would convert this boat for a tiller. Most sailors consider a wheel as an upgrade, though, so it is neither here nor there in my mind.
If I were you, not that I am, I would look for a fixed-keel boat with a shoal draft. I wouldn't waste time with a smaller boat where you will immediately feel cramped. I would also be leery of anything trailerable if you intend to keep the boat at a slip or mooring. The fixed keel should give you more security in the relatively higher wind areas where you may be sailing. Do not be concerned about your ability to handle a boat in the 5,000 to 8,000 pound range. Like somebody said, sailing is the easy part of the learning curve, the boat systems and maintenance is the hard part.
I think there are a lot of Starwind 27's down in your area and at a good price, I wouldn't hesitate. They are a speedy little performer with a lot of nice attributes for a small cruiser. Just find one in good condition, that is important. You want to sail when you buy the boat, not get stuck on the hard with repairs.