Hi John,
I haven't been smoking a pipe for 25+ years but I thought I'd throw in my 2 cents... Remember, rule no.1 in this hobby is that everybody has their own opinion and you're gonna get as many answers as there are people answering you! Anyway, this is what I would have said to myself if I could travel back in time to the day I decided to get my first pipe...
1. Like a lot of people told you, I would start with a Missouri Meerschaum corn cob pipe. My favorite is the Country Gentleman (straight). It has a hardwood plug at the bottom of the bowl and with a straight pipe it will be easier to get a pipe cleaner in there. Try to avoid the really cheap corn cob pipes and get at least one with a hardwood plug at the bottom. Also, Missouri Meerschaum is made in USA. Corn cobs are inexpensive, they are very easy to smoke and forgiving for the beginner. It will not gurgle and is easy to relight. I would stick to those for a few months and then maybe buy an estate briar pipe from a trusted retailer. Cobs are ok and I had (and still have) great smokes in them. You will see, with time and experience a briar pipe will probably give you a better smoke but don't expect it to be a gigantic revelation once you smoke the first bowl in one of them. It takes time and practice, that's all.
2. As far as tobacco, I would get 3 tins or maybe 4. A good aromatic, a virginia, an english and a burley. Here is what I recommend, those are part of my regular rotation and are recognized as major players in their own categories:
Aromatic (flavored tobacco): Dan Tobacco Sweet Vanilla Honeydew (if vanilla is your thing) or Dan tobacco Devil's Holiday (more of a wild berries type of taste) those two tobaccos really taste like what they smell.
Virginia (citrus and fresh cut sweet hay notes): Orlik Golden Sliced or Dunhill Flake
English (think camp fire smell, meaty but round): Dunhill Early Morning Pipe or Mac Baren Latakia Flake
Burley (think raisins, nuts, fresh baked bread and pure tobacco flavor): Solani 656 Aged Burley Flake
Again, remember this is my own opinion. Some people will disagree with me but those are my main go-to blends and they never disappoint.
BTW, the reason why that Cohiba made you sick 20 years ago is probably for 3 possible reasons. You may have smoked it too fast, you may have inhaled the smoke or it might have been a counterfeit and who knows what was in it... But cigars are great too and are a passion of mine as well. You should reconsider smoking one some day!
3. Filters. I don't use them and I don't inhale the smoke. I think they are used by a majority of European countries but smokers there tend to inhale. (again, this is my opinion. I might be wrong)
4. Get yourself at least a golf tee for a tamper but I would spend the $2 and get myself a Czech tool. Most pipe smokers use them on a regular base. Get yourself some pipe cleaners to absorb moisture during the smoke and to help cleaning your pipe once you are done smoking it. A regular size Bic lighter is what I use most times. I have other fancy lighters but I don't carry them with me by fear of breaking them or losing them. The only thing for a Bic is you have to know how to hold it and angle it properly to avoid scorching the rim of your pipe. Hold upside down, light away from the pipe and bring the flame closer from the tobacco only when drawing air.
5. Other than that, be patient, give yourself a lot of time, smoke when relaxing. Don't count the number of times you relight. Don't be too self-conscious. Puff slower than you think you need to and pack the pipe looser than you think you have to.
This is just a foot in the door for you. It takes year to perfect your techniques, discover new pipes and tobaccos... But it is a fantastic hobby and you will make real friends within our community.
I hope it helps and as I said a few times already, this is only my own opinion.
Olivier