Tent
For cycle touring, I chose a free standing tent.
This means I can set up anywhere, and also use my inner tent as a mosquito net indoors or on hard surfaces.
After years of having a cheaper tent, I have spent more money to get a lighter and more weatherproof tent. Its really worth spending whatever is required to stay dry in the rain and reduce the weight you carry around - especially if you travel around for a while.
I stay dry when it rains for days, and my tent stays put in the wind. But, don't expect the more expensive tents to be perfect either. I have found issues with every tent I have owned.
Its better to leave later from your campsite than to pack up a wet tent. Its heavy, and you will have to unpack it again later on to dry it out - or it can get mouldy. Once your tent gets mouldy, theres no getting rid of it, or the smell. If you have no choice to leave, then spread out your tent as soon as you ca - aircon buildings such as bus terminals or airports are good for drying out things (Ask first about where you can do this - you will get friendliness instead of glares).
However, I find it quite enjoyable to spend a morning drying things out then packing up light, dry stuff that I dont have to unpack later,