Granada vs. Leon vs. "North Nica" - any advice?

Both Leon and Granada are mainstream-tourist-stuff which you are not into, Leon has still a a more local atmosphere, Granada already overrun by tourists, using the US paying system in restaurants with tax and tips on their bills, triple prices...
Esteli less touristy, consider visiting the canyon and eco-finca nearby.

What about some more adventure, and cross to CR via Ometepe, Solentiname islands, San Carlos/El Castillo, and boat across Rio San Juan to CR at Los Chiles, then to La Fortuna/Arenal?

If not, then skip SJDS, and head to NW Pacific beaches in CR, far nicer and more nightlife, then to SJ.

SJO is not in downtown San Jose, but NW of the city in Alajuela, 30 minutes taxi/bus. San Jose is not the end of the world, plenty to see and do and enjoy if you have a late afternoon to kill or a night for a dinner/partying.

If you do head to the north of Nica, I would head there first, then make way south...

Second making a leg of the trip via Lake Nicaragua ferry. Less often used by tourists and you can stop off at Ometepe and/or Solentiname. We did this route last year N bound from Arenal to Grenada. Long boat ride all the way up the lake, but beautiful dawn approach to Grenada.

thanks #1 and #3, advice from people who have actually done some travelling in nicaragua is welcome. i personally feel that the north of nicaragua is a great place to visit. i have been back many times and will continue to return.

i would drop granada, esteli and matagalpa have a lot to offer.

Logistically (and with your time limits) Granada will be the easiest.

It is certainly also the most touristy option of the three.

I liked all 3 places well enough,though i didn't spend a lot of time in the north the people were great and the temperature was a lot milder than in Leon or Granada.

As a city Leon has some beautiful buildings,good food and also friendly people....

Really i don't think you can go wrong with these options ;-)

A. Granada and leon are similar architecture wise. But have historically been different politics wise. Granada is full of luxury tourist and cater to the older, retired crowd. Leon has a lot of young eco- loving volunteer-loving people. Hippies as many people say. Both are very touristy, with granada being the most tourist frequented place in the country. I would recommend leon over granada for sure, but if you cant stand mainstream tourist stuff you may wanna skip both.
They both have decent surroundings with things like volcanos to hike, etc.

B. If your plan is to spemd time in granada, ometepe and south, you will have a hard time fitting esteli and the north in plan. However, if you choose leon first, you could do leon, then esteli or the north, and then head south to ometepe, etc on your way to costa rica. I would try to maximize your time by starting on one end and going to the other. Doesnt make much sense to go south then head north, then head south again, etc.

C. If you are averse to tourists/mainstream stuff i would recommend skipping all your suggestions, as the places you mentioned are all the highest tourist destinations. Except ometepe. Its a tourist destination sure, but i still highly recommend it as its the one place that deserves it. You can stay in, or outside of managua, and do day trips from there to chocoyero reserve, volcan masaya or mombacho, even do a daytrip to granada, leon, or masaya if you want, do a day trip to the beach in pochomil, las penitas, montelimar, tola, etc. I dont understand why everyone runs out of managua so quick. Its not pretty and the city itself isnt super amazing, but its perfect as a base for day trips, and the surrounding area is excellent., esteli is good with the estanzuela reserve nearby. If you are in the north you can check out somoto canyon too. There is also the much less traveled path to solentiname islands or rio san juan, but both take a chunk of time and wont allow for muktiple days in multiple locations.

D. Anywhere is better than san juan del sur if you arent into tourism like you said. Its second only to granada in tourists. Its pretty though

Stick with Granada and drop Leon. Leon has some things to see but is a working city and I found it boring . I even went to the coast for dinner to liven it up. Granada was nicer, yes more touristy, but sometimes that can be a good thing. Plenty to see around there on day trips too.
If you are going to Estelli, do it first then head south. You can catch the bus to San Jose in Granada or Rivas. Take Tica Bus, they make the stops. This would have much better logistics for your trip.