Just have top notch insurance and get an umbrella to cover yourself.

So exactly what rehab will condo cover? 

We have an application for one of our apartments with 2 tenants. Our minimum requirement for credit score is 580. 1 of the applicants credit score is 558 (this person makes majority of the income) and the 2nd person h...

I would focus on screening your tenants for background, credit, and income to try to avoid an eviction and excessive damage to your property to minimize your turnover expenses and vacancy loss.  

I'm concerned that if I bring up the matter of withholding security deposit to cover the costs , they might cause more damage to the house prior to vacating this month. 

The HOA told me that though that's a bit low, they will allow it as long as I use area rugs so that 80% of the unit is covered by rugs or carpet (I have carpet in the bedrooms).  

It's best to set expectations upfront and ensure they're going to cover all of the areas that you need to see.For inspections, while it depends on what your main goals are (e.g., price vs. quality & comprehensiveness), you can usually find plenty online.

How much was the umbrella policy if you don't mind sharing$1347 annual for a $2M policy covering 3 cars / 3 drivers (one under 21), primary residence, one STR and an old pontoon boat. 

Which means, as long as the total gross rent covers, the anticipated principal interest taxes, insurance - you will have a greenlight for funding, good luck!

Possibly cover the cost to evict as well.