My recommendation is to go to a dealer and tour some units of both types. It's pretty easy to see yourself in the unit your touring - hang out in the dinette, on the couch, bed, etc. If your getting a motorized RV, you will either have to tow a car, rent something or be stuck at the camp site.
If you have a General RV dealership within a reasonable distance, check their used selection. Then, once you find a platform you think you would buy, start looking at Craigslist, and RV Trader. Look at dealerships too, but check prices on NADA and never pay the asking price.
On any particular unit, make sure you can check it out while it's plugged in and can have all systems demonstrated - AC water heater, Fridge, water pump, etc.
Check the date codes on the tires - especially a travel trailer. ST tires can look good while being at the end of their lives.
Backing gets easier and yes, a pickup truck is a handy item to have for home use.
Don't rush and come back and ask questions.