Could we deduct 50% of the security deposit as a new tenant placement expense when the previous tenant breaks the lease? 

The buyer doesn't perform you typically have to just go file an eviction just like with a tenant except when is the bond for deed filing eviction it will usually take about 45 days to complete the eviction process.I've done a few over my time both buying and selling and it's not that difficult.

Just looking at timelines, since we wouldn't receive the bill until after the security deposit was due back to the tenant after move-out.Thanks, 

What are you guys using to secure your vacant properties?

@Jake Parks - If you're pooling money together and providing a return for people/there is an expectation of profit for someone else and that other party is not involved in the decision making/management of the deal , then you are creating a security and the answer to your question is a resounding yes.The big thing you have in your favor with partnering up with family and friends is that you have a relationship with these people already and that's the biggest thing that the SEC is looking for.

Both sides are leased at low rent with no security deposit.

I could sell one of my properties (condo) use, that money for flips in Atlanta within the next 1-2 years build up additional funds to acquire an apartment complex, and to grow my portfolio, but I want to hear from some experienced investors and what they would do if they were in a similar position.Current Picture/Portfolio: Property 1: Condo (Atlanta, GA 30328)Current Rent = $1550/MonthUtility Reimbursement = $200-300/MonthHOA $383 (In line with HOA's for other communities) Purchased June 05th, 2015 and resided in property until Jan 22nd, 2017 (Total of 1.64 Years)Lease Started Jan 23rd 2017 and Lease Ends on June 30th 2018.Current Equity 135,000 (Purchase Price)  - 85,000 = $50,000Current Comps Similar Properties are selling for $155,000 to $170,000Current Mortgage Terms: 15 yr Fixed 3.325% Monthly payment of $996 (Includes Insurance and Property Taxes)Anticipated Total Earnings if Sold at End of July $64,500 (Sell Price $155K) to $78,500 (Sell Price $170K)  Property 2:Town-home (Peachtree Corners, GA 30092)Current Rent = $2000-4000/Month (AirBnB) 60-70% Occupancy since November of 2017Purchased July 28th 2017 and currently residing in basement house-hacking with my younger brother.HOA $325/Month Covers, Water, Lawn Maintenance, Sewage, Security GateCurrent Equity 336,000 (Purchase Price) - 265,000 (Remaining Loan Balance) = $71,000Current Comps Similar Properties are selling for $345,000 to $360,000 due to private/public school ratings going up shortly after purchase.Current Mortgage Terms: 30 yr Fixed 4.326% Monthly payment of $1823 (Includes Insurance,PMI, and Property Taxes.)

Here's a sample of fine print:“Borrower shall occupy, establish, and use the Property as Borrower’s principal residence within 60 days after the execution of this Security Instrument and shall continue to occupy the Property as Borrower’s principal residence for at least one year after the date of occupancy, unless Lender otherwise agrees in writing, which consent shall not be unreasonably withheld, or unless extenuating circumstances exist which are beyond Borrower’s control.”Different lenders have different "fine print" statements that may be more grey and confusing.

They seem inexpensive but not sure if that is what I would want as they may be less secure for larger storms.I know I am asking a lot of questions so I appreciate any help you guys can give to a new investor!

I did the deal more to secure the land which is literally across the street from a major OC university.