There is a good reason for your conflicted state.  Both areas are liked, but by two separate groups of men.  Those working downtown like a lunch break or more.  Those in the metrowest areas hate driving downtown and problems with parking.

And some of us will see you anywhere in eastern ma 😊

I know it is a lot like California in a sense that Boston proper is a lot different then North Shore/Waltham. Though I know a lot of ladies don't mind. Gentleman usually don't like to travel though..

I think Alluring Amber does not consider you a gentleman.

Both areas are good! A lot of men work in Waltham or Burlington as well as downtown, you could do a few days downtown and a few in Waltham to accommodate people who can’t go too far from their office during the day.

I’m not familiar with Burlington/Woburn but it seems like there are definitely guys there looking so it’s worth potentially staying there too. In the case it doesn’t get many responses it’s easy to stay downtown an extra day, hotels are fairly affordable here unless there happens to be a conference )

Another chance for me to post about finding such things.
http://www.boston.gov/visiting-boston
and this site
http://www.signatureboston.com/events
lists events and anticipated number of attendees.  
Some dinky little 3-day show or meeting with 200 attendees shouldn't strain the Boston hotel system.
A 6-day event with 25,000 attendees could do several things (a) bring in a lot of out of town clients spending a couple of days in Boston, some of whom might be looking for some nearby R&R between meetings or (b) drive down the availability of cheap rooms during that meeting.  
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Anyway, no matter what city you tour to, if you're not a native following the news and events every day (sporting events, playoffs, a visit from the President or the Pope, ...), look for the local Visitors and Events calendars to understand why hotel rates are high or low or why there are many or few pre-bookings.
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Good luck!

Me personally I only traveled into Boston for one woman. As others said us outside the city generally hate the city. Traffic in/out, parking, getting lost in maze of one way streets with 1/2 of them closed vs Burlington, for example, hotel right off 128, easy to get to, plenty free parking. Only downside for me is rush hour so I plan dates accordingly. Plus city is 2x farther on top of it all

Good discussion here.

My 2 cents

With the traffic and logistical issues getting in and out of Boston I only play there for a special lady. Between traffic, trying to find parking, seems like dates usually run late and the hotels mandating room keys for elevator use its time consuming and challenging.

I play anywhere from Newton to Peabody and even if it takes longer to get there.

I am surprised there aren't more ladies in the casino area. Maybe that coming.

If you work downtown, your inclined to doing a lunch or after work appointment. Your less inclined to go out to MW unless you live there bc traffic is brutal.  

If you work out in metro west, you probably prefer after work appointments. Weekends are probably also better bc locals can fit a tryst in around chores. Your also less inclined to head downtown bc parking is as much as the appointment.

I’ve done it. My favorite was when I lived in MW and worked in the city, I had the best of both worlds. I currently live and work in the city and never make it out to MW.  By the time I get home and get my car, I’m ready for dinner and a whiskey. It’s unfortunate bc I miss out on some of my favs if they don’t book in town.