That would probably be the easiest way.
You could also consider getting some kind of transport (taxi? hitchhiking? not recommended but only a suggestion) to one of the Jewish settlements, either Shavei Shomron or Kedumim (no transport from Nablus would be able to enter the settlement so you would have to get out on the road), and a bus from there to Kfar Saba, from where there are buses and trains to Tel Aviv.

Few people pick up hitchhikers in the USA, its unsafe. Try to find some fellow campers and arrange transport. Rhinebeck is in the Hudson Valley and quite an elegant weekend destination, they do not look kindly at hitchhikers around there. Once you get into the Wilderness area you may meet up with other people who help you out but I would definitely look into hiking groups, outdoor groups, or just rent a car.

Bishkek - 1 night

Unless you are arriving late don't bother staying in Bishkek. Just get straight on the road, if you want to see Bishkek do it all at the end

North Issyk Kul lake - 2 nights

If you have to do the north side just do 1 night, then spend longer on the south side (more interesting and less touristy).

Karakol - 4 nights

Decent amount of time assuming you plan to do a multday trek. If you just plan to spend 4 days in karakol it's about 3 days too long.

Jyrgalan - 2 nights

Good choice. Decent amount of time for some day trips.

Kaji-Say - 1 night

Not sure why you picked kaji-say? It's fine but not particularly interesting. If you want somewhere on the beach there are other choices (kaji-say is 2km or so). Bel tam yurt camp is perhaps a better choice for just beach. Bokonbeavo is a good choice as a base to do trips from.

Song-Kul - 2 nights

Sounds fine. Better to hike up over Uzbek pass and stay with a nomad family than drive up to the "tourist village" imo.

Arslanbob - 1 night

How do you plan to get from song kul to arslanbob in 1 day? I don't think this is possible. Also arslanbob itself is not particularly interesting, it's more of a trekking base. You would not really have time to do any trekking. I don't really see the reason to spend so long travelling to just sit in arslanbob village for a couple of hours.

Sary-Chelek - 2 nights

If your doing this on public transport you will spend the best part of a day getting from arslanbob to sary chelek village (not sure it has a name but all the accommodation is outside the park entrance gates, you won't actually be near the lake). From the village it's a substantial drive up to the lake, I'm not sure there are any buses but you can hitchhike up.

Suusamyr - 1 night

I tried to make the journey from sary chelek to suusamyr on public transport and it's very slow. I actually ended up overnighting in toktogul as wasn't sure I could make it in 1 day. Remember if you are coming via public transport you have to hitchhike or walk the last part from the main road. Even if you have private car you won't get to suusamyr until quite late, then you will have to leave reasonably early the next day to get to Bishkek. There's not really anything to see in the village so it seems unnecessary visit unless you are trekking.

Personally I think you are trying to cover too much ground in too little time. Sary chelek and arslanbob are way out the way. Sary chelek is nice, but there are plenty of other nice lakes without going all that way. Arslanbob is not particularly great, there are nicer villages and better trekking elsewhere imo.

The highlights of Kyrgyzstan are the nature, trekking, and culture so I would focus more time on them then driving around trying to visit lots of places.

With 17 nights you could easily spend the whole time just around issyk kul, jyrgalan, kochkor song kul areas. If you don't like as much trekking just add sussamyr valley (Bishkek - suusamyr - kyzyl oi - song kul), it is perfect route for acclimatisation however there is no public transport in this valley so you need to hire a car or hitchhike).

I was also considering hitchhiking to save money on travel. Apparently it is very doable in South America?

You might survive. I don't know. Probably your phone and your money would be stolen, maybe your luggage too.

Starting in November, would the weather be ok?

It will be rainy season on the southern coast of Brazil, and also in the Andes mountains in Peru/Bolivia. So yes, you will get wet some places. Might be a little chilly in Buenos Aires, but not like Europe in winter.

Can you guys recommend any must do experiences, things I cant miss when I am there?

Going through Paraguay/western Brazil, try to stop in the Pantanal region at some lodge where you can see the famous wildlife. Much better than the wildlife you can see most Amazon places.

I would stay close to the Las Pailas entrance of Rincon de la Vieja so El Sol Verde (where we stayed) or Hacienda Guachipelin would work (I already mentioned both hotels above). It depends on your budget. El Sol Verde provided transport to the park.

I have only been to Rincon de la Vieja. I have not been to Bijagua. I suggested it because I have been researching that area. We usually travel by bus and it seems like we would have to rely on some kind of transport to the entrance of the park. I am sure tours will be offered but we like to do things on our own. I have heard there is a hostel that has a shuttle service. Or we would try to hitchhike. We usually figure something out when we are there.

Can you guys recommend any must do experiences, things I cant miss when I am there?

Is your Google not working? 'Please tell me all the things I should do or see based on absolutely no knowledge of my tastes or interests'.

I was also considering hitchhiking to save money on travel. Apparently it is very doable in South America?

It's pretty bloody daft, is what it is. Not recommended.

then fly back from Venezuela

So you are blithely unaware of the current situation in Venezuela, vis a vis personal safety and cash as well as the issue of airlines there? Quelle surprise.

May I suggest that you do some basic research, maybe read a guidebook or trawl through the older posts here first? You will get much better advice if you do.

Good luck! I suspect you will need it.

Cueto is interesting, especially if you arrange (through Bob) for his Cuban significant other to take you on a walking tour of the town. She's the provincial cultural director and way better than anybody else I've had for a guide. Everybody knows and likes her so they'll make you welcome as a friend of hers. She speaks excellent English. Fidel's birthplace, Biran, is barely an easy hour bike ride from Cueto over a back road. But no place to overnight in either Biran or Cueto. The down side is that the highway between Holguin and Cueto is quite nasty for traffic, although not so bad if you get out out of Holguin City by 6 AM. Hitchhiking is not a good option for Cuba but s Bob pointed out, taxis are cheap.

Candy is definitely the go-to person for Gibara, which is a nice day's bike ride from Holguin. But don't try to go and come back same day. Same is true for a trip to other places on the north coast--Las Bocas, Playa La Heradura, Guardalavaca, and Cayo Saieta--each of which is worth visiting if you've got the time. Casas at all of them except Cayo Saieta, where there's only the villa.

You can rent bikes in Holguin. See https://www.profil-cuba-reisen.de/en/bike-rental-in-cuba
Not sure about Santiago. Do take a lock, as I don't think the rental company supplies them. The main problem with doing a day trip from Santiago by bike is getting out of town, which takes forever, and traffic is fierce until you do. If you're a super jock, La Gran Piedra makes for a good day trip. Easier is the ride to the fort or Playa Siboney on the east side of the harbour, or Playa Verde on the west side of the mouth of the harbour. Not a lot (if any) foreign tourists at any of those places.

NZ is an awesome and beautiful country. We were just there for a month in Feb on our yearlong RTW trip and had an amazing time. Truth is we wish we had spent another month, so you'll probably be glad you allocated two months. While my wife and I had each other, we ran into plenty of people around our age (late twenties early thirties) traveling solo and even gave a solo female backpacker/hitchhiker a ride. She said she felt safe and had mostly been hitching around and met lots of friendly people. Have an awesome trip!