I Would Like Your Input

This is really an impossible question to answer, there's way to many variables and the bottom line as to you losing money depends on how much you pay for them.

If I had a crystal ball that could tell me things like that I could have been rich many, many years ago.

I believe that nice currency will go up in value over the years but you may still lose money on what you bought.

Collecting currency is not at all like collecting Silver or Gold coins, if what you have in coins are not rare dates then everything will depend on the spot price of Gold and Silver. And of course you could lose a lot of money on that kind of thing, some don't think so but all you have to do I ask some of the guys that bought Gold and Silver in the 1980's and held on to it into the mid 1990's then tried to sell it.

I don't look at currency as an investment, I look at it as an enjoyable hobby, if what I collected goes up in value that's fine, if not that's ok also.

I believe that once you start looking at currency collecting as an investment it becomes less fun and more of a job. There are many other ways that are probably a sure thing as an investment other than currency collecting.

I would bet that there very, very, few currency collectors on this forum that are cashing in big time on there collection, in fact there probably not even cashing in small time.
Bill Collector

All of the notes you listed are always in demand so if you are thinking of selling them in the future you should only buy them in high grades because most collectors who will be in the market for those notes are going to want them in a high grade,IMHO. Here is a thought, narrow down those four notes to two notes and get them in a higher grade then if you bought all four notes in a lower grade.
John1

You might want to put together an educational set and then go after the 1899 Chief or Bison note.

Even on the high grade notes -- There are bigger differences in price....follow some auctions listings etc...get to know the variation in price between a RAW note / graded 64 and 67 etc as it can vary 30 to 50%.....Most importantly learn to grade a raw notes as it is a dicey game.

Fwiw, I collect errors, fancy sn's and short run star pairs...just to give you an idea. There is a BIG diff in price (I am sure the same will apply in your situation) that may get you a graded 67 for less than a raw note...been there done that.

Good luck and let us know how it goes. The educational series is always in high demand and they would be awesome to have in the higher grades. Like others have said, I would start off with those 2 first.

You might want to get a ball park price of each note in the XF+ price range (like completed ebay sales, dealer sheets, price guides, etc) and then see what you can get, based upon how much money you have to spend. Even if it takes you 5+ years, it is something that can be done, it will just take more time to do it. Which is part of the fun too.

@LB-I absolutely love currency. IMHO Celyon is completely correct. Learning to grade currency will pay off big time in the long run. It will help you not get burnt purchasing raw notes.
Grading currency was not offered at the ANA's summer seminar this year but they did a 2 day seminar before the ANA in Denver in May. I live in Ohio right now and for me to fly out there and stay for the two days of the seminar and for one day of the show it totaled about $1,300. But if you are talking about purchasing high grade 'investment quality' notes it's worth it.

I'm not sure if you do any vest pocket dealing but, one thing that I've noticed after learning to grade currency is that if you really learn how to grade really well there are a lot of instances where you can pick up good notes priced at lower grades than they are.

Hope this helps!