Welcome to the forum pnolans!
For several years, we had a reproduction 1950's Kit Teardrop Trailer, it was 4.5'x8'. When I was preparing to go on the road, I seriously considered using our teardrop, or even building a smaller one to tow behind my Prius (e.g., 3'x8'). But, as it turned out, I realized I could live out of my Prius just as easily as I could live out of a teardrop. And, I've been a part-timer in my Prius now for over 6 years. We no longer have the teardrop.
You asked for some pros and cons, so here are some off the top of my head.
Teardrop w/Tow Vehicle Pros:
- Dedicated bed (teardrop is basically a bed on wheels),
- Enough overhead space to sit up and lounge in bed,
- Dedicated kitchen (most teardrops have a galley in the back behind a hatch),
- Plenty of storage space in your tow vehicle for clothes, toiletries, food, and camping gear,
- Teardrops are usually light and easy to tow,
- Teardrop community is very helpful, outgoing, and friendly (check out tnttt.com).
Teardrop w/Tow Vehicle Cons:
- During bad weather, need to go between teardrop and tow vehicle for supplies (clothing, toiletries, food, gear),
- Also during bad weather, may feel claustrophobic if spending most of your time lounging in teardrop,
- Also during bad (windy) weather, tent/awning/covering will blow away or get torn apart,
- Getting in and out of the sleeping space is awkward (need good knees and/or good flexibility),
- When getting into teardrop bed, no place to put dirty/muddy/wet shoes for easy access in morning (without getting bed wet/dirty),
- Teardrop is an extra vehicle to license, insure, and maintain,
- Backing a teardrop is an extra challenge (due to short distance between wheels and hitch),
Other thoughts and questions:
- Depending on your personality, this may be a pro or a con -- Teardrops are cute, they attract attention and questions. For example, when getting gas, we always planned on spending at least a half hour extra in anticipation of questions while fueling up.
- Make sure you have a top vent/fan or some other method for air circulation while you sleep in a teardrop, otherwise you'll run low on oxygen and have lots of condensation.
- As with towing any trailer, make sure weight is evenly distributed with the heaviest items over the axel.
- How much electric power will you need? We had a house battery that was charged while we towed our teardrop. If you are camping a lot (and not driving), how do you plan to charge your house battery? Solar panels on your tow vehicle?
- If you can, go to a teardrop gathering to learn from those who use them. Information on gatherings at tnttt.com.
- If you can, go to a Rubber Tramp Rendezvous (
RTR) to learn from those who live out of their vehicles (next one is in June near Flagstaff, AZ).
The years of using our teardrop helped prepare me for living small out of my Prius. If backpackers can live for months at a time, using only what they can carry on their back, you can certainly live out of a teardrop should you find that's your best solution!
Enjoy the planning and preparing ... I think it's fun stuff!
Suanne
) And I'd prefer to live in the woods than on the streets. 
