E-Bike questions:
I'll address this mostly to you Stephen but will put in some generic stuff that other people may need to consider. If I think of anything else I'll edit it in.
First check your local laws to make sure they are legal and what requirements you have as a rider/owner. I listed some of our Ontario ones earlier in the thread. You might find some restriction you can't live with (some won't wear a helmet for example).
Second ask yourself what you want to use it for. Make sure the model you buy has the carrying capacity which is not just the weight but the storage. For example my first bike had a trunk that was too small for a bike helmet to fit in. Another do you want a bike or a trike? There are trike versions made specifically for shopping with a "truck bed" behind the seat for carrying.
Third, storage and charging. Where are you going to do them? In your case you can probably put it in a barn or shed but it has to be asked.
Fourth: Roads. You really want a hard surface. A significant layer of gravel is not safe (I nearly wiped out hitting such a patch the day I bought the 2nd bike). Muddy country roads are very bad also. Asphalt or concrete is what you want to ride on.
To ask the dealer:
Range: The more weight you are carrying (including cargo and the heaviest clothes you may wear while riding) the lower your range will go. It is NOT linear, range drops faster than weight increases (at least in my case). Unless your weight plus cargo is under 175# assume a significant degrading of range.
Weight capacity: It appears that the higher capacity the slower the drop in range as actual weight increases. The target weight they use when calculating range is 175#s for every bike I have looked at, so compare your weight plus expected cargo to that to decide if you are likely to make the range (ask the dealer specifically what he thinks).
Alarm: Both my bikes have a "key chain" remote which not only controls the alarm but also can be used to start the bike remotely - or stop it. My sisters however don't have the remote and the alarm disabling can be done more easily by a theif. So just having an alarm doesn't mean much. You really want the remote if you can get it.
Power assist mode: Can you use both pedals and power at the same time? This extends your range and lets you handle uphill climbs better. Hills can really be draining on the battery, pedaling can reduce that significantly. My second bike has this feature the first doesn't. Pedalling 170#s of bike when the battery is dead is a task most would avoid, I've done it with the first bike repeatedly for significant distances.
Pedals: If the law requires that you keep the pedals on look for folding pedals). It is quite easy (voice of experience here) to give your leg a painful whack if not more with the standard pedals.
Wattage: The higher the better (within the law) here they sell 350 and 500 watt. My first bike was a 350 the second a 500. Acceleration and hill climbing are better with the 500.
Voltage: Most bikes I have seen are 48 volt (both of mine and my sisters are 48s). I just recently saw some that are 60 volt. The higher voltage enhances hill climbing. The 60s also use 5 batteries not 4 and that extends their range.
Lock: I bought a proper motorcycle wheel lock made by the people who make "The Club" for cars, it is much superiour to the ones provided with the bikes I have seen.
Kickstands: Some have 2 some one. The side leaning stand is easier to use but not as stable. The other requires strength (that I know you have) to pull the bike up onto it, smaller lighter people can have trouble with it.
That is good for a start.