For TLC standards, I would dissolve them in whatever gives the best solubility. I find that it does not matter what your TLC standard is dissolved in, so long as it is suitably volatile the solvent will evaporate before you ever run the plate.
For columns, to avoid potential funny business, I prefer to dissolve my sample in the mobile phase with which I will be running the column. Obviously to get the tightest bands you want to keep the volume of solution you are loading to a minimum (i.e: high concentration). The number I've been quoted and which has worked well for me is "less than 2% of the bed volume".
To load: pack your column as usual (slurry pack please, dry packing is for delinquents), then drain the solvent down until it is level with the top of the bed (or sand if you are using a sand layer on top), then use a pipet to gently dribble your solution down the sides of the column. Start as close to the bed as you can get and be as gentle as possible, the last thing you want to do is to disturb the top of the bed (another reason why a sand layer is usually a good idea). Drain until the solvent is again even with the top of the bed, then dribble a few mL of mobile phase in and drain as before. Repeat with solvent 3 or 4 times to get it good and loaded, then gently pipet solvent in until you have about 5 cm of solvent above the bed, then pour more solvent in until the column is full. Now elute as you normally would.