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I'll be setting up my first aquarium (50g) soon and wanted some opinions/feedback on my fish choices. Live plants will also be added, eventually.

Bolivian Rams
Yoyo Loaches
Harlequin Rasboras
Blue Gouramis
Also considering some Red Cherry or Rudolph shrimp

I (of course) won't be adding them all at once, but wanted to make sure there's no compatibility issues down the road. Also, which ones would be the best to start with?

sounds pretty good except the yoyos might attack the shrimp. here is a stock list with those fish

2 Bolivians
6 yoyos loaches
12 Harlequins
1 Blue Gourami

I would suggest a bristle nose plec or ottos for algae control.

Welcome to Fish Profiles!

Your list sounds great. The only thing that troubles me a bit is the blue gouramis. They have a tendency to be a bit nasty to each other. Some can get very agressive. Some people have had success keeping several together, some haven't. Instead of blue gouramis, I'd suggest getting a couple of pearl gouramis. Same size, but nicer to each other, and IMO, a lot better looking.

To start cycling, I suggest a big school of harlequin rasboras. At least 10 to get it going. They are small and hardy. Just remember to keep a close eye on water parameters. If you wanted, you could also do a fishless cycling, and just add pure ammonia to your tank, therefore not risking the lives of any fish.

Thanks for the welcome and suggestions.

Now, can I add a few plants right away (~5), all of them (~10), or wait until my tank has cycled? Between my wife and I, we know enough about water chemistry and fertilizers (we both work on water quality projects); I just want to know if there will be a risk to the plants and/or fish if I put all the plants in now.

Definitely add the plants now. The cycle won't harm them, and the plants will actually help the cylcing of your tank along.