I am looking for advise .We want to move away from security deposits and charge only Move-In Fee.

S8 Challenges:1) Voucher holders not having funds for application fees or security deposits2) Tenants trashing properties, killing ROI3) Tenants not paying their portion of rent or utilities4) Tenants not cooperating with ongoing S8 requirements or inspectionsAlso, you stated in your initial post that you'd be buying turnkey rentals.

We were unable to secure offers within a reasonable price point.

Here's what I was thinking...Can I ask him for a deposit to hold now that will then be used as his security deposit? 

I do not think it only matters whether you were an employee or an independent contractor- I believe most states would look into how the security deposit funds and rental payments are held/ by whom.  

Now if this is a full 6 month MTR then yes, I would change the lease dates a week to secure the booking.

It will also detail other various impacts such as traffic, security etc.. 

The experience gained and the equity built can set the stage for future investments and a secure financial future.

Oceanfront homes are extremely limited and commonly ask $1.6M+-$2M++ in the center of town it can be very difficult to secure an STR permit due to saturation (active neighboring vacation rentals) requirements.Lincoln City offers a variety of oceanfront home options, the challenge with oceanfront STR's in Lincoln County is that actively licensed STR's do not transfer and would generally be subject to a lengthy waitlist.

It also costs extra for maintenance and security.