You should be OK, as long as your realize the following...
I suspect, when all is said and done, your 214WSD is going to be closer to 4400 or 4500 lbs empty, when you roll off the lot. The "dry weight" on trailers is just that...bone dead dry; no battery, no LP gas, no options (even the "mandatory" ones).
You'll need a WD hitch, I believe the Tacoma is rated for one, and with the weight of the hitch and a loaded trailer, you are going to be really close to your tongue weight limit, even packing lightly. Most people don't realize exactly how heavy even "packing lightly" really is. You also need to keep an eye on your Tacoma's gross vehicle loading...the payload that is being applied to the truck's over all weight. With two adults and a tongue weight of 550-600 lbs, you won't have a lot of load carrying capacity for the bed of the truck. The payload capacity is right around 1200 lbs; that has to cover a fulll tank of gas (the "factory weight is calculated with a 150 lb. driver and 1/2 tank of gas), options on the truck, other occupants and the trailer loading.
You don't say where you're from or where you'll be towing, but, you've already realized you are going to be "underpowered" for the hills, so, that won't come as a rude awakening
Can you do it? Yes, as far as the numbers go. Would you be happier with more tow vehicle, certainly, but, we all have to start somewhere and in today's economy, as long as you aren't unsafely loaded and you drive with the knowledge you are close to your vehicles limits and act accordingly, less can be quite adequate. Just know you and your rig's limits, as you won't have a "safety cushion" of excess power and loading capability to fall back on if things get "hairy".