The "baskety" moulds are more for soft cheeses and ricotta and feta. Cheeses that usually don't get pressed, but are stackable so one fits inside another while pressing themselves by stacking these moulds with curds.
The one with holes and straight sides are more for cheeses that get put in a press and are usually sold with a "follower" top plate. One can apply much more pressure to these moulds than a baskety mould.
To make recommendation, we would need to understand how big of cheeses you plan to make, type of cheese you are making... And how "traditional or authentic" you want your cheeses to be. There are a good handful of cheese supply places that have moulds with descriptions of size, dimension and cheese type it is designed for.
You can easily start with a tomme mould that will do most cheeses if you are not picky about the shape of your cheeses. Eventually get more moulds more specific to your needs later.
With regards to the cheesecloth thing... I make sure to pull the cheesecloth tight from underneath by pulling up on the sides... For a smooth top I simply just use a single flat layer or two across the top... Not bunched up ...the excess being outside of the mould...and I don't use too big of a cheesecloth for the press. For smoother cheeses one can remove the cheesecloth and just press "bareback" without cheesecloth for the last few hours. There is a cool new netting used for cheese presses instead of cheesecloth which is not as bulky.
Hope this helps