The perceived benefit to the investor is they either get the inflated price, or if the deal goes "bad" and the tenant defaults they get to keep all the deposit money and rent and all that.

We embrace S8 applicants, but screen them just like any other applicant.Many have an entitlement mentality and try to leverage their S8 voucher by pretending to be helpless:1) A percentage won't apply because they expect a landlord to waive application fees for them.2) Many cry broke and expect a landlord NOT to charge them a security deposit.3) Many of those same S8 tenants trying to avoid paying a security deposit, won't make an effort to call the list of nonprofits we send them that will pay their security deposit if they apply.4) A lot of them try to avoid paying for utilities.

I have done small things like switch from glass wine cups to acryliic ones that look like glass and take a damage deposit of $250 that helps mitigate small things breaking that are over $50.

The problem is that they do not usually give this to new people and/or people that do not have big amounts deposited into their accounts.I'm also CT based. 

If they are changing jobs, they need the new job first and you need to paychecks or offer letter with salary or maybe even the first two paychecks at the new job, depending on their level and income.Ask them about deposit and rent. 

The fighting over them is endless.

You can get some estimates from contractors for what they charge for big ticket items like to renovate a bathroom, renovate a kitchen, replace the furnace, replace the roof, etc.All wholesale deals should have free and clear title and you should be able to see the sales agreement before submitting the earnest money deposit.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Yes, endless nightmare

You have decent cash flow that you'll continue to accumulate, which you could put toward a deposit later for another property.