You have quite a few selections based on the topics you requested. Here are some:

Financial:

-Venice: A Documentary History, 1450-1630 edited by David Chambers, Jennifer Fletcher, Brian Pullan. Good collection of primary sources.

-Gold & Spices: The Rise of Commerce in the Middle Ages by Jean Favier.

-The Commercial Revolution of the Middle Ages, 950-1350 by Robert Sabatino Lopez. A very important landmark text in the study of Medieval trade. A bit out of dated at the moment, the text covers the rise and development of many Italian city states and what elements made them perfect for developing mercantile empires.

*The Economy of Renaissance Florence by Richard A. Goldthwaite. An excellent text with a ton of detail regarding how trade worked in Florence at the time: prices, items, contract explanations, etc. Highly recommended.

-Commercial Agreements and Social Dynamics in Medieval Genoa by By Quentin van Doosselaere

Society:

-Muslims in Medieval Italy: The Colony at Lucera by Julie Anne Taylor.

-Renaissance Florence by Gene Brucker. Excellent read for a quick crash course on how Renaissance politics (specifically in Florence) fueled the art industry.

-Forbidden Friendships: Homosexuality and Male Culture in Renaissance Florence By Michael Rocke

-Immodest Acts: The Life of a Lesbian Nun in Renaissance Italy by Judith C. Brown

-Venice, A Maritime Republic by Frederic Chapin Lane.

-Italy in the Age of the Renaissance : 1300-1550: 1300-1550 edited by John M. Najemy

Art:

-Painting and Experience in Fifteenth-Century Italy: A Primer in the Social History of Pictorial Style by Michael Baxandall. A nice, detailed study of painting evolution throughout the 15th century in the Italian City States.

-The Patron's Payoff: Conspicuous Commissions in Italian Renaissance Art by Jonathan K. Nelson, Richard J. Zeckhauser and Michael Spence. A more recent and up to date study in the relationship between patron and artist during the Renaissance.

Figures of the time:

-The Letters of Machiavelli : A Selection by Niccolo Machiavelli, University of Chicago Press.

-Machiavelli and His Friends: Their Personal Correspondence by Niccolò Machiavelli, Northern Illinois University Press.

-Communes and Despots in Medieval and Renaissance Italy, edited by John E. Law. This one touches on some of the more controversial policies that affected the politics of the city states..some hurt more than others.

-The Devil's Broker : Seeking Gold, God, and Glory in Fourteenth-Century Italy (Frances Stonor Saunders) (a lighter read that does a decent job at explaining how mercenary culture damaged some core elements of the Renaissance Italian military structure).

-Cosimo de` Medici and the Florentine Renaissance by Dale Kent

Documentaries:

-The Medici: Godfathers of the Renaissance done by PBS. Every Renaissance studies teacher I ever took showed at least part of this..I have seen it a few times. Includes interviews with some of the top historians of the time. Of course, like all documentaries, it is important to check facts before making assumptions. Very good in general tho. It is available online for free at the PBS Youtube page: https://www.youtube.com/channel/SW7JPZboRLQjc

Overall, that list should be good at getting you started and making you understand the fundamental structure of politics, finances, art and how they affected each other.