First off, thanks for any help/suggestions folks can offer, I'll try to describe my situation and questions, be feel free to add other things I should be considering or "dumb" things that I'm thinking! 
I live on the water in S. FL (Stuart area, for those who are familiar with the water) and have a dock with a 20K lbs boat lift that can handle about a 29-30' LOA boat. I currently have a 2005 Bayliner 225, which is JUST long enough to be able to board (it's actually somewhat terrifying, but besides the point) that I'm enjoying, but slowly realizing that it's the wrong boat for my area. I've always owned bowriders in the past, but never boated on water like we have here (in the ICW) and the distances are just so vast (especially with all the no-wake zones). Not having a head or a protected compartment is a real problem, and it's limiting my enjoyment of being able to use and take the boat out.
Anyway, I'm looking to upgrade to a larger boat, and would like to get some opinions on what others think. Here are some of the criteria that I really want in my next boat (in rough order of importance):
Cabin w/head
Generator
Fuel injection (I'm done with carbs, they are a PITA)
Windlass (I spend a lot of time at anchor, there's a lot of fun places around here to anchor up)
Dual Engines
I'm somewhat conflicted on the last point (dual engines); I'd "like" to have them for the redundancy, but, more importantly, for the steering; this is a tight area with a lot of boats; I'm a bit scared of a 26+ foot boat with a single engine in tight quarters. However, at the same time, I'm also not to keen on the idea of 2X the repair/maint bills. I'm leaning towards duals, but would like to get others opinions on it as well.
In general, this is the style of boat that I'm looking at:
http://www.boattrader.com/listing/2004-Sea-Ray-280-Sundancer-99523010
http://www.boattrader.com/listing/2005-Four-Winns-288-Vista-98680534
http://www.marineconnection.com/web...m Beach-FL?args=preowned--?condition_id=10426
So, some specific questions:
Is there some other style of boat I should consider for my use?
Could I run these boats through the Stuart inlet (on a good day) safely?
What do you think about the single vs. dual engine decision?
Anything else that I'm missing for my use?
Out of the boats above, what do you guys think?
Are there any outboards that I should consider (it's shallow here, the ability to tilt all the way out would be nice for beaching the boat in some areas)?
Feel free to answer some, all, or none of the questions.
Thanks for the help!
I live on the water in S. FL (Stuart area, for those who are familiar with the water) and have a dock with a 20K lbs boat lift that can handle about a 29-30' LOA boat. I currently have a 2005 Bayliner 225, which is JUST long enough to be able to board (it's actually somewhat terrifying, but besides the point) that I'm enjoying, but slowly realizing that it's the wrong boat for my area. I've always owned bowriders in the past, but never boated on water like we have here (in the ICW) and the distances are just so vast (especially with all the no-wake zones). Not having a head or a protected compartment is a real problem, and it's limiting my enjoyment of being able to use and take the boat out.
Anyway, I'm looking to upgrade to a larger boat, and would like to get some opinions on what others think. Here are some of the criteria that I really want in my next boat (in rough order of importance):
Cabin w/head
Generator
Fuel injection (I'm done with carbs, they are a PITA)
Windlass (I spend a lot of time at anchor, there's a lot of fun places around here to anchor up)
Dual Engines
I'm somewhat conflicted on the last point (dual engines); I'd "like" to have them for the redundancy, but, more importantly, for the steering; this is a tight area with a lot of boats; I'm a bit scared of a 26+ foot boat with a single engine in tight quarters. However, at the same time, I'm also not to keen on the idea of 2X the repair/maint bills. I'm leaning towards duals, but would like to get others opinions on it as well.
In general, this is the style of boat that I'm looking at:
http://www.boattrader.com/listing/2004-Sea-Ray-280-Sundancer-99523010
http://www.boattrader.com/listing/2005-Four-Winns-288-Vista-98680534
http://www.marineconnection.com/web...m Beach-FL?args=preowned--?condition_id=10426
So, some specific questions:
Is there some other style of boat I should consider for my use?
Could I run these boats through the Stuart inlet (on a good day) safely?
What do you think about the single vs. dual engine decision?
Anything else that I'm missing for my use?
Out of the boats above, what do you guys think?
Are there any outboards that I should consider (it's shallow here, the ability to tilt all the way out would be nice for beaching the boat in some areas)?
Feel free to answer some, all, or none of the questions.
Thanks for the help!