Venue help!!!

I can tell you that a Friday wedding will be inconvenient for your guests, especially if they are out of town. Sunday early wouldn't be as bad. Missing work is hard for me, so consider that.

I would definitely think very carefully about how realistic it is that the majority of the guests you want there will be able to travel to the wedding (e.g., considering cost, time off, season of the year scheduling conflicts, etc.). You might even talk with some of the key guests and VIPs and ask them what they think. There was just a post this week from a very sad bride who is ending up with a much smaller wedding than she expected/planned/paid for because so many guests declined -- mostly because they'd have to travel 4-6 hours. She's really disappointed and wishes she'd made a different choice for the wedding location, but it's too late now.

If you'll be happy with "whoever can come," and it's the right location for your tastes/budget/etc., then go for it. But if you'll be sorry that people who mean the world to you cannot attend, I'd consider other options. Too frequently I feel posters on this forum respond to this type of question with, "It's your wedding! Do what you want and those who truly love you will be there." I think in a lot of cases, that is really bad, and potentially misleading, advice. I can absolutely adore you, but if I can't afford to travel or I can't take the time off work or from other obligations, I'm going to have to decline your invitation. As the bride/couple, you'll need to be okay with that. Good luck! It's a tough decision.

I would book in whatever town you & your FH want to get married in. I would necessarily pick somewhere just because it is close to more of your guests. It also needs to be convenient for you.
I agree with Allie on the Friday wedding situation. If you have a lot of out of town guests, Friday’s would be hard. But Sunday’s would also be hard because people would need to leave to get back to work, unless they are fine taking off. I would try to find somewhere that is available on a Saturday since you have a lot of out of state guests. Are you dead set your current wedding date? If you’re flexible, that may help a lot in your venue hunt.

I would go with your gut about the venue. Discuss it with any people that must be there (best friends, grandparents, etc) that are out of state and get their opinion. I have a ton of out of state guests and chose a Friday wedding to save costs. Yes, people may have to take off work to come, but let that be their choice whether to attend or decline. A majority of our out of state guests have accepted and we were pleasantly surprised. If you do something local (keep in mind it will be easier to plan) just make sure to send save the dates early so those people can plan accordingly.

Next question, what are your thoughts on holiday weekends such as Memorial Day or Labor Day? It solves the issue of people having to take off work since we would do a Sunday wedding. However, I know some people don’t like traveling during holidays and I also live in a beach town, so hotels may be an issue for availability and price. I’m so discouraged because I feel like no matter what, it will be the wrong decision. Even if we moved the venue closer to our families, there would still be an issue because mine are in Southwest Virginia and most of his are in Maryland.

Again, it's probably most helpful to talk with your VIPs about the options you're considering and ask for their honest feedback. For some people a holiday weekend is awesome because they have extra time off, for others the idea of traveling in holiday traffic and paying inflated holiday prices is a deal breaker (and in some professions, it's impossible to get time off on holidays). Before you reach out to get guest input, I'd call some hotels and see what their availability and pricing is for the dates you're considering, so when you talk with friends and family you can give them a realistic idea of the cost & time commitment -- on a holiday weekend, many properties may have a two or three day minimum reservation requirement. If you're thinking about next Memorial Day, they might already be booked, as many people book their same favorite holiday locations every year. (We live in So Cal, and I definitely understand both the good & bad of living in what nearly everyone else considers a resort/vacation destination.) I don't mean to be a wet blanket, but I'm all about trying to make informed decisions. Without the specific details, as a guest, the idea of a "vacation wedding" in your resort location can sound awesome and I'll plan to come, but if I later can't afford it or make reasonable travel arrangements, I might end up cancelling on you. Hopefully, with good information, people can give you an honest, realistic response. Good luck!

If there are venues in your town that you like, I would go with that option. Are there nearby airports? Are you willing to wait/push back your date if a venue is booked out pretty far. Fridays and Sundays are good options as well, but if you choose to do that, just make sure you send out Save the Dates well in advance. Taking time of to travel on top of a friday/sunday wedding could be a deal breaker for some guests.

As long as you're okay being prepared for a smaller turnout, I'd book the local venue!