So, I'm two days shy of paying my security deposit on a wee storefront in the historical downtown area where I live. I'm moving my 2-year-old wholesale/retail bakery business out of kitchens where I stay dually employed, and into my own brick-and-mortar. Goodbye forever, sleep! Downtown storefronts are very in-demand here, and subsequently unreasonably priced for the most part, with the landlords all having reputations for wanting to consume as much $$$ as they can while spending as close to nil as possible. It's late October now; the present tenants are leaving December 31st; the landlord has agreed to replace all linoleum flooring; all of this considered, I'm guessing I'll get into the building to start re-outfitting it halfway through January at the earliest. Here's my conundrum: I'd like two months, or at least one to one-and-a-half rent-free to get this place going. A previous employer/owner/baker suggested requesting three months and settling for two. I can't imagine not getting at least one. However, given the high demand of the space, I'm worried this will be used as unfair leverage against my request. I'm sure many of you have already been in my shoes, and I'm looking for: your thoughts about how reasonable a two-month rent break is? suggestions as to how to approach the topic with the landlord? how to reinforce the validity of my request should the landlord immediately say no? thoughts on whether you would consider a refusal a dealbreaker? would this be a red flag for you? winter killed us in this area last year; there's a good chance this year will be the same; should this even be brought up regarding the accessibility of the space during the time i am moving in, or should this be considered irrelevant? thoughts on signing a lease while there is still an operating business inside the building for two months vs. waiting until the business has exited and a walkthrough can be done? the property could be in completely different shape in two months, no? Also: When is bringing someone with you to a lease/security deposit/commercial rental opportunity considered appropriate? My boyfriend happens to be my contractor/painter/investor/future-employee and I would like to include him in the discussion, as I feel his input could be vital to negotiating our needs. Appropriate? Inappropriate? All of your thoughts, tips, suggestions would be so so appreciated. I'm pretty sharp, and I'm very articulate, but sometimes I get weak treading water in business negotiations, and I could really use some factual and experience-driven reinforcement. Thank you to everyone in advance for your input.