Some heists are quite difficult to pull in time, so plot your course carefully. Also for the covetous countess missions be sure to keep what laundered shipments you get from other quests.
On the other hand jewelry chests in buildings and some NPCs in a certain town are sometimes isolated and can be picked off easily without bounty. You will almost always get caught pickpocketting unless you have ledgermain leveled and Light Fingers 4/4, also you'll almost always get seen stabbing the contract target which sits near other NPCs most of the time. For the repeatable ones I recommend skipping the pickpocket and contracts and only going for the jewelry box and covetous countess, and sprees respectively since those have higher reputation increase with lower bounty. Note that the latter can be done multiple times a day. You need to do the daily quest - Heist and Dark Sacrament respectively - for a bigger increase in that rank, and repeatable quests like pickpocket, jewelry box, covetous countess and contacts or spree respectively for smaller increases. Thieves Guild and Dark Brotherhood main quest progression is linked to your rank in the faction, as well as doing the perquisite quests.
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