Help for an Old School Audiophile

I'm 56 and I've been in this hobby since the early 80's and have a modest system and have amassed a collection of about 1500 LPs, 500 cds, and 400 cassettes.  Between two different older hard drive tower cases I have probably about 10,000+ songs on iTunes and I keep those tower cases around thinking one day I'd like to put those songs on a cloud - although I totally don't know what that entails.  I have the free Pandora on my iPhone and still regularly listen to FM radio and have an aversion to paying for satellite radio when there are good stations in the Philadelphia market that I listen to.

Last week, I went into a local hifi shop and listened to a bookshelf pair of powered Dynaudio speakers that you could hook a laptop up to but also had RCA outputs to hook up a phono preamp to and the salesman was playing music thru his phone.  He had Tidal and also mentioned other names that I forgot the name of.  When I saw what he could do thru his phone, it kind of made me feel a little foolish for having all of these albums, tapes, and cds.

I don't watch a lot of tv these days except for sports and I'm amazed at how my 24 year old daughter can watch all this stuff with Netflix and by streaming stuff and I'm still paying lots more each month for cable.

I'm not gonna go out and change it all tomorrow or the next day but I guess my questions are this:

1.  What's the best way to get educated about all of the different options that I have?
2.  With regard to all the music on iTunes that I have, is it better and more cost effective to put that music on a cloud or should I just subscribe to Spotify, Tidal or some other music format and just throw out the old tower cases?
3.  Can I assume that most people who have music servers are using that for music in lieu of actual music collections?  Or do most people have both?  
4.  If I were going to one day purge my collections but still wanted access to all the music I have now, what would be a good - modest - step by step game plan?  
5.  Is it better to get a USB turntable or analog to digital converter and start converting my LPs to computer files or is that a waste of time?

The actual collections and all the gear can take up a little room, but they are cool to look at too.... on the other hand, having the extra space and being a minimalist has it's own merits.  I'll never own a kindle either :)

BTW:  (My current system consists of:  Tandberg 3012 int amp, Thorens TD125 mk II turntable, Kyocera D-811 cassette deck, Harman Kardon TD302 cassette deck, Creek CAS3140 tuner, Oppo DV970 cd/dvd player, Fostex B-100 BH speakers, custom 45 SET tube int amp)

Thank you in advance for all of your kind comments and suggestions, 
Lou