@Brett Dudley the inspector for any buyer should catch the roof needs replacing and any other major issues, which should lead to the buyer renegotiating/lowering their offer price to cover these.

Once the issues are solved (i.e. permits are issued, debts are paid off, etc.) the lien goes away.If you do your due diligence, hire a General Inspector and a Roofing Inspector so that they can give you THEIR assessment of what's going on. 

Getting the inspection also affords you access to the inspector/plumber who is looking at hundreds of sewer lines everyday, probably of that same building age. 

Now after more than a month waiting, I got an email from the Bank stating that an inspector found a man on the porch, and he assumed the house is occupied.

I am trying to figure out how I can find a contractor or inspector that I can trust to view and walkthrough potential investment properties and would give me honest estimates, etc.

Home inspector, property manager (some states require various licensing), admin at a realtor office, contractor / trade apprentice, landscaper, home painter, lender, wholesaler, or co host / arbitrage STRWorking at a Lowe's or Home Depot would be good too.

We feel very confident in our underwriting, but given the jump that we made from SFH to an apartment building, we want to ensure we're not missing steps in our DD/inspection plan.Here's our current plan:1) Have a general inspector complete a Property Condition Assessment.2) Have specialists complete an evaluation of the roof, electrical, foundation, and heat source (2 steam boilers).3) Review financials, all leases, existing service contracts, rent roll, tax assessment, rental certificate, and 12 months of work orders.Here's what I'm not sure about:1) Are there DD items (specifically those that we would request from the seller) that are not captured within #3 above that we should be requesting?

Profits are not always guaranteed, so make sure you build a reliable team of agents, lenders, inspectors, and contractors.

I was unprepared for the havoc inspectors can cause.

As they should be, it takes more effort to wait for inspectors, make repairs, ensure rules are adhered to, etc. and that should be factored in.