I’ve heard the first few months are frustrating because it’s hard not knowing the ins and outs and how to do stuff, and I really want to avoid it because I want to be a reputable agent people take seriously. 

Instead of allowing tenant and landlord to work it out before it damages a Tenant’s record i.e. court date is set, tenant understands there's consequences, an agreement is reached, eviction is avoided… however a moratorium changes this dynamic... now we will still file a notice of eviction while attempting to work out a payment plan with the Tenant however, the difference now… is that a new agreement has been reached and if for some reason the Tenant is unable to fulfill the new much more forgiving agreement and then still refuses to downsize... evictions, credit filings and garnishments are imminent and will surely ensue immediately after the moratorium. 2 – It’s already started most Tenants just don’t know it yet – What happens to vacant units when there’s moratorium in place?....

I left my job in IT years ago in order to restore and renovate the house after it was significantly water damaged from a broken pipe.

For an investor, having a project manager/contractor who (1) understands their business goals, (2) can do great, on time, and inexpensive work, (3) can communicate with the city for permits, (4) have a network of reputable roofers, HVAC, electricians, plumbers ... this is an invaluable relationship for an investor, particularly those investing in properties that will need reno work done (flips, or BRRRR deals, etc.). 

This is downside protection.2) Security Deposit: In the event of eviction, the landlord can keep the security deposit as collateral rent and damages.

So far, 2 have reassured us on the phone, not in writing that no lump sum will be requested at the end of the term, and that our credit will not be damaged..

If the tenants don't change that one, it could actually result in maintenance calls and/or potential damage to the HVAC system. 

Regarding ARV, I don't see any noticeable damage but assuming once under contract I will need an inspection done and then a contractor or two to price out for me?

I'm just not going to replace those things in a rental unless they're damaged, and if they're damaged then I'm charging the tenant for it.  

A security deposit is not meant to carry a tenant, it is to mitigate damage.