The landlord has 30 days to send a letter to the former tenant returning the deposit or explaining why he is retaining it or a portion of it.

At this point my retainer had run out and it was going to cost another $100 or so to have them file the writ of restitution plus filing costs.

Given low likelihood of long term tenancy due to their demographic, we wouldn't take a loss now in the hopes of retaining them going forward.We've already given them opportunity to renew at a partially mitigated escalation and did not get a response, so we're not expecting them to stay.

Also If any one entity owns greater than 10% of a project (50 unit project) based on your 5 retained, you're still not getting a Fannie or Freddie loan.  

Can anyone here recommend a surveyor and/or engineering firm who can guide me through the land division process, create the new plat plan and help sort though the possible need for a new retaining wall on the south end of the lot?

I don't think anyone needs to allow tenants to walk all over them, but being fair and seeing their point of view is not only the right thing to do from a human perspective, but is good business because it retains tenants and move/out/make ready for new tenants always costs time and $$$.

Or is it better to just rely on a good handyman or repair person on staff/retainer/rolodex.As @Joe Splitrock said, I have found that the adage of "they don't make them like they used to" seems to apply to most mechanical and electrical devices these days.

For a young family with more energy and muscle than money, it's a good deal.

Actual Lenders Title Insurance states;CONTINUATION OF INSURANCEThe coverage of this policy shall continue in force as of Date of Policy in favor of an Insured after acquisition of the Title by an Insured or after conveyance by an Insured, but only so long as the Insured retains an estate or interest in the Land, or holds an obligation secured by a purchase money Mortgage given by a purchaser from the Insured, or only so long as the Insured shall have liability by reason of warranties in any transfer or conveyance of the Title.

@John Pflederer Have you considered bringing a handyman on via some sort of retainer?