So, do a land contract instead.

So I have a seller interested in Sub to but the loan officer told here he wouldn’t finance her second home.

So many lenders out there will bait and switch. 

If so, would love to hear which lender you went with.

If so, then you should expect to be honest with them.

I know you are already active in the the Chicago real estate game so excited to see you jump in here as well.If there is any way I can help, please let me know!

So basically Ill be paying 12K a year for property taxes on a 320k building.

There are definitely pros and cons to each so I figured I would just lay out a few benefits and personal thoughts: Small banks/brokerages:Pros:- Some regional knowledge of the market- Possibility of more creative lending guidelines with bank specific programs- Sometimes they have competitive rates for their areaCons: - weak balance sheet (more strict on some guidelines, no wiggle room, inability to be flexible or grant exceptions because they cannot afford to hold less than perfect loans)- Can't scale with clients to different markets- Usually limits exposure to individual investors (they don't want one investor to be too big of a portion of their balance sheet)- Lack of experience with multiple solutions (tend to have 2 or 3 loan products they sell and are too niche to provide tailored solutions)Large banks/brokerages:Pros:- Large compliance departments that understand individual market guidelines (typically each state has specific lending guidelines that augment the national baseline)- Ability to scale into multiple markets with same lender (licensed in many states)- Impossible for individual investors to "outgrow" a large bank's balance sheet (not concerned with one investor's concentration)- More lending solutions available for different scenarios- Often comparable or better rates given the game is volume basedCons:- Can be more difficult to get fast responses if the bank/brokerage does not have good follow up systems in place (or if the underwriting/processing staff gets overwhelmed)- Bad large banks can feel less like a relationship and more like a cog in a factory (less personal)Overall, I have worked from both and worked with both as a loan officer, branch manager, and as an investor/client myself. 

So I am trying to understand how to negotiate cash closing.

The rate varies depending on the state in which the property is located so I can't give you specifics without having more information.Capital Gains Tax: When you sell a U.S. property, you may be subject to U.S. capital gains tax on any profit.