I've been an on and off smoker for years, I've been smoking a pipe for a couple years to cut down on the amount of tobacco I introduce to my body(prevents me from smoking every time I get in a car or step outside, still a nice way to get a fix and relax in the evening).

Money has been a major issue until now that my wife and I both have decent incomes.  I've had the occasional cigar here and there but as I said... money has always been a major issue.

On the 4th a friend gave me an Acid Blondie (I know, I know, "They make cigars for men too" etc., I even lit it with a bic lighter, the horror!) and it made me remember how much I like lounging back and smoking a nice cigar(yes, I say nice, though definitely not what I'm used to, and likely won't be my go to, the flavor was decent and it burned impressively well).

Looking for a nice budget friendly list to start picking away at, eventually a small humidor will likely be on that list but for now I'm planning on burning as I go as I haven't officially started the new job yet.

Also where does one look to get the best deal on cigars?  Local or online?

It's tough to beat online prices.  My go to is cigarpage.com  Right now, they have pretty much every stick they sell on sale in a 5-pack, cigarpage.com 5 packs for the 4th

You can store your sticks for cheap by using a cooler or tupperware container with a Boveda pack, no fancy humidor necessary.

jrcigars, cigar international, famous smoke shop, thompsons,

For a humidor can use a tupperware container and a boveda humidification pack. Or those clear jar type containers with a snap on lid if you want to store 25 or less cigars. Inexpensive humidors don't really seal all that well.

Rubbermaid or one of these will do for a humidor rubbermaid for larger size etc... No need for something fancy. They have some that come with a Boveda pack or just the humidor. These will hold about 20-25 depending on size.

A lot of sellers are low on inventory for some things. People with time off and nothing to do, plus people that got a stimulus apparently bought cigars with some of it.

Cheap jar humidor

I have bought some “seconds” that I really like locally.
About $4 so I don’t mind too much if I don’t get to finish them.

Fuente “short story” gets recommended a lot and are pretty decent for $6 or $7.

Drew estates has some seconds called factory smokes for a few bucks as well.

(Prices all depend)

Thanks for the link.  Got in just in time to stock up.  Unfortunately I can't yet afford the 'good stuff'(and likely never will be able to at the rate I smoke).  I'll treat myself here and there but that gave me a really nice stash of fillers for inbetween.

I do have a 'fancy' humidor already(honestly no idea why, or where it came from, or if it'll hold decent humidity so we'll see) but grabbed an acrylic jar for infused cigars.

Just getting into cigars myself, and these were recommended to me. So how's it for a 'starter' pack? Should I smoke them while I reload...lulz??

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Holtz and cigarbid are also really good online sellers. I would encourage you to support your local brick and mortar stores. You can meet many great people in the cigar shop. Here's a short list to get you started:

Arturo Fuente Hemingway maduro
Punch Gran Puro
Padron 4000
La Flor Dominicana Cabinet No. 5
Tabernacle No. 142
Henry Clay War Hawk
Oliva Serie V
Charter Oak maduro

You're a seasoned smoker so I wouldn't worry about hopping into the stronger cigars. Construction this year has been horrible. I can't count how many $10+ cigars I've smoked this year that were potatoes and completely un-smokable.
Get yourself a good cutter and torch lighter. Do not buy anything from Xikar. They used to be great, but suck now.

I bought from a local store. I think I paid a fair price for what I see online.

My dad recommended the Glen because he's a single malt guy and like the Glen once in awhile. I tried the Olivia and I love it. It has this pepper like flavor and the aroma is pleasant imo. Lights easy with my torch, and has an easy draw and even burn.
I'm only looking to buy some decent cigars to puff on 1-2 times a week at most. As far as humidor I was just gonna grab a glass jar off my shelf and put moisture pack in it. If that's not sufficient, let me know, and I'll just find a decent humidor.

Oh, and thank you for the suggestions. I'll keep this sub'd and get them over time and try all of them.

https://kohnhed.com/category/best-cigars-list-by-price/

Cigar International isometimes runs deals on humidor and cigar packages.

My wife was looking around and ask me if I want this:

https://www.amazon.com/Cutter-Lighter-Sharpening-Engraved-Guillotine/dp/B07JGS368B/ref=sr_1_46?dchild=1&keywords=cigar+cutter&qid=1610657565&sr=8-46

what you guys think?

Look fine to me, the Fuentes would be a good one to try as well.

Perfectly ok to have a cigar while reloading, as long as you're just depriming, sizing, trimming, chamferring.... pretty much anything without powder involved.

Darn...I wanted to dance in the powder while lighting my cigars. Shit.......

Cigarbid.com

JFR Lunatic rabusto

Alec Bradley Tempus Nico

Oliva Serie V Melanio

CAO Flathead Sparkplug and V660

Colibre is what I use. Buy once cry once. I got the double cutter in copper. It's a brick but cuts better than any other cutter I have ever used.

https://www.amazon.com/gp/product/B0779G414N/ref=ppx_yo_dt_b_asin_title_o07_s00?ie=UTF8&psc=1

Don't feel bad OP. an acid blondie was the first cigar I ever had back in 03-04. When the pool hall sold cigars. I'd start off mild to mellow cigars. One of my favourites is the drew estate Kentucky Fire cured, it's more of a medium strength.

I’m using CigarPage almost exclusively for my LFD Double Ligero Diggers.

Anywhere from $12-$12.50 before tax, here in Miami, closer to $17 when I go home to Los Angeles.

I’ve just ordered 10 more for $90 with no tax and free shipping. My last 15–two weeks back—were $127 to my door.

That’s a savings of about $4+ a stick.

Chris

Almost anything that can be sealed makes a good humidor. Colibre v cutters are awesome for around $50 or get a Colibre firebird For 12-20. Find a good torch...2 to 4 flames for starting and a single for touchup. Or matches work good if you are a patient soul.

Also, check out Cigar Monster great way to sample a few at a time.

Start a log, paper or phone ap, notes on what you liked, taste so when you want it again you will.

Try different lengths, gages, wrappers, growing regions.