have been to Nicaragua a few times before by air and driven much of the country with my family, know Granada, Managua, San Juan del Sur, Corn Islands, etc.
Vehicle
I took everything in a self-contained new cargo van big enough to stand up in, a heavy duty truck. Most important feature - limited slip rear differential. Not so great at ground clearance but only had one problem getting on and off the roads which are better than we think but have drop-offs and rarely shoulders.
I got a cargo van with no side windows for privacy, rear door windows with security grilles inside, installed 3M security film on windshield, door windows and rear windows. Took extra door glass for both front doors, extra oil and air filters and bulbs and fuses. Also 3 sets of tires on rims and a floor jack and air compressor with plug repair kits. Tires are 10 ply commercial.
My only vehicle problem so far was losing the glass on right side mirrors when swiped by semi yesterday coming north into Guatemala. Duct taped the assembly back in place and looking for temp mirror glass of some sort.
I received absolutely no attention to the white cargo vehicle from any police or military, who are everywhere except for some double takes at my California license plates. I was pulled over for speeding in El Salvador coming north but got a friendly warning. A few papers checks in different countries. They all liked the dog.
Problems in Nicaragua with vehicle.
Permits must be renewed every 30 days. In Managua OK, would be an overnight trip because it takes 24 hours. Every so often, I don't know when, must be renewed by reentering country. Information from expats I met.
Supposedly if vehicle permit is expired and driver is caught, vehicle is impounded with unknown return procedures.
I can't stay there all of the time so decided not to leave van.
Best approach to bring in long-term vehicle is to become pensionado (retiree) permanent resident status, which is it's own process of which I know little. Supposedly available at age 45 with evidence of permanent income, requires some documentation from home country (police clearance good record).
Allows free annual registration of vehicle.
If I do it again I would get in US 4 door 4 cyl manual transmission 4 whl drive pickup, small Nissan, Toyota, Isuzu. Mainly because there is no camping, kayaking, bicycling almost anywhere in Central America. Can't be done - nowhere to do it. I saw one roadside park coming north, a military memorial with benches. There are no parks, public spaces, anything. Even the nature preserves are barbed wire enclosed. Private resorts would be the only thing and you'd have to rent a cabin. There is rarely anywhere one could even pull off the road at all, few shoulders, no parking, lots of pedestrians and buses everywhere.
And I wouldn't bring much stuff. You can't use it on the road. You can buy things there that are nice, believe me. One overland book says bring twice as much money and half as much stuff.
No vehicle over 10 years old allowed. No vehicle in Nica sharing anything with anything you get in US so you are risking quite a bit if damaged or crashed.
Nicaragua sells you mandatory liability insurance at customs at the border $12 for 30 days. They insisted on including my bicycle on the policy.
Guatemala, El Salvador, Honduras I had no insurance.
Mexico requires insurance to get in. I used Sanborn's in McAllen Texas, to cross at Pharr, Texas. $125 approx complete coverage for 5 days.
Got in trouble at a paper check in central Mexico bc all these countries put the day and then the month for dates and Sanborn's put the month first, so traffic cop claimed it was expired before I bought it. Talked him out of it. His main concern was getting wifi on his smart phone so it could translate for me.
I am in the process of getting insurance to get back into Mexico going north.
Not that happy with Sanborn's online before trip, Johnny at the main office sent and received forms by email, dropped it completely and I had to start over in their office at McAllen.
Every country will make you get a temporary vehicle permit to get through it.
You will have document checks at random places. You will also have to get it canceled when exiting the country.
Mexico is the most complicated but good for 6 months.
They require a bond on your credit card when you get it and they credit your card back when you leave the country with the vehicle. Everyone checks all the id numbers very carefully and often on all the papers. If you have a lease or car loan you will need written permission from the lien-holder on your vehicle to get the vehicle permit (according to the books and Sanborn's Insurance, I have a clear title so didn't apply). The bond varies with the age of the car, I think $100, 200, 300 or 400. I paid $400 for the new vehicle. It's quite a process - they put a sticker on your windshield with a microchip in it and remove it when you leave.
In general, US driver's license, vehicle title and passport are required for vehicle permit at aduana (customs) and all your information must match. I think Mexico was $35 for the permit, Honduras and the others less or nothing.
Everywhere you go in every country wherever you park there will be a guard, usually private, armed with shotgun or machine gun. Normal. Parking elsewhere is not good. Parking on a road is never possible anyway. Streets sometimes but highways in cities a demolition derby.
The driving is really crazy and the tumulos, sometimes signed, sometimes not, speed bumps are beyond belief and will destroy your vehicle and rearrange your load in ways you cannot imagine. You will learn to scrutinize the road surface so carefully you will be doing nothing else.
Trailer
I would never pull a trailer in Central America / Mexico.
My large van fits into a normal parking space but it's huge.
Getting trapped into narrow streets, stopped traffic, herds of cows, insane semi and bus drivers happens all of the time, and even on the actual Pan American Highway (Carretara), which can turn from a high-speed new paved separated 4 lane into a pot-holed 5 mile an hour gravel pit covered in people and vendors in an instant, no exits or turning.
The Guatemalan death wish bus drivers or Mexican 53 ft semi trailers will clip you somewhere and never notice. There are no driveways, shoulders, parking, sidewalks, just crazy traffic everywhere. Turn arounds exist in a couple of countries on the highways but most not.
GPS
Any smart phone without a plan talks to satellites for GPS apps. Must download country or area map as well as app. Mexico has a good one we used. Central America we used two, for Android, saved our lives. One from Kaart, (maps a couple of dollars) the other from Nokia called HERE maps (free).
Any questions about GPS let me know. They're tricky but saved our lives often, esp the big crazy capitals. DON'T use google maps. Lead me into illegal Guatemala entry, cost us three days return. Stay on the Pan American.
Central America puts huge US style signs on every damn creek and bridge in their countries. They never sign the roads, streets or highways. I bought $300 worth of real maps and used them. I'm on my way back to California, entering Mexico.