You've had a lot of responses on this, let me add a few more thoughts as someone who made the same jump (LE to airlines) 2.5 years ago. I'm a little older than you but you're old enough to be more or less in the same boat. You can likely remember when LE was a dream job and something that you really looked forward to doing, now it's just a job. Airline flying will be the same thing- eventually it will settle in to being just a job. Granted its a job that I really enjoy, but it has it's downsides like any job. Just be prepared for that when the honeymoon period wears off.

Drama? You're going to find that in any line of work. It's less so than at the PD but it's still there. There are a lot of 25 year old kids (I'm at a regional, but the LLCs are not far behind that curve) on their first job and fresh out of mommy's basement, who think they know everything there is to know. There are crusty old timers who hate everything in the world including themselves. There's everything in between. Mix them all together and there is going to be some drama. That said 90% of the people I work with are great, even the CAs that I fly with who are barely old enough to be my kids. When I walk into the crew room and close my eyes it sounds like I'm right back in the squad room- same personalities, same loud voices *****ing about the contract, the union, management, blah blah blah. The environment felt strangely familiar the first time I walked in the door.

Speaking of home- you're going to be home less since you'll be on the road for between 3-6 days at a time, with 3-5 days off in between (rough average.) Make sure that the family can handle that. Now here's the upside- when you are home, you are truly home, fully present and not stressed. For most of my LE career I had jobs that were 24/7/365 on call, so even your off time is never fully your own. Plus you bring home all the stress and issues from the job (read Dr. Gilmartin's book if you haven't.) At the airline, once you set the brake at the end of a trip and go home, you are truly off duty. I don't take any stress home, I don't need a day to decompress, I don't answer a phone on my days off, I don't think about work much at all until it's time to go back for my next trip. In other words, the quality of time that you are home is much better. This can be a big deal in some families.

Training- the training model at the airlines is very similar to that in LE. You show up on day one and come out the other end as a newly type-rated pilot who knows your company books inside and out. Just like a fresh academy graduate, you know everything and nothing at the same time. You then go through a period of field training (we call it IOE or some variation) where a seasoned FTO-type teaches you how to apply all that knowledge "on the street." You then go back for periodic refresher/ in-service training to practice skills that you are likely to never need in real like, but nevertheless need to keep sharp. Most pilots go their entire career without a real engine failure, just like most cops go their entire career without firing a shot in anger. But both of them must maintain those skills just in case today becomes "that day."

While we're on training, think about this when you're looking at ways of building your time. Buying yourself 1000 hours in a 152 is one way to get it done, but what is the quality of that experience? I'd guide you towards actual flying employment where you will get some real world experience in the big-boy IFR system. Airlines expect you to show up on day with with this background, and without it you will really struggle. I work part time in the training dept at my airline and I see this with new hires. The more real world experience you have the better prepared you will be. Not to mention, the older you get the more calcified your brain becomes and the harder it is to absorb new material. You're not that old yet but old enough that you will start to notice that when you "drink from the fire hose."

You mentioned looking at specific airlines based on their proximity to your home and the ability to drive to work. I think that is a great plan- being able to drive to work and not have the added stress of commuting (via airline) to work is a huge quality of life factor. The standard caveats apply- bases come and go so you have to do your research. Some bases are more secure than others, and what is plan B if your base closes.

There are some folks who will tell you that you haven't succeeded unless/ until you have a job at a legacy. Hogwash. I think you have the right idea of finding a mid-level job and settling in, if it balances out the money/ family/ QOL equation. Hell I'm at a regional and I'm pretty content- upgrading soon and will be making pretty good money (better than I ever did at the PD) and driving to work. With single digits of years left, I may well just ride it out where I am (assuming my company still exists, which is always a gamble.) There is very little that is certain or stable in this business. Like you I got back in to aviation after getting out in leaner times (early 90s) and I settled in to LE with its job security. One of my favorite comparisons is this- LE is a great career, but it's a lousy job. Airline flying is a great job but it's a lousy career. You've seen enough in LE to know the difference.