It is normal to not have access to units until you are under contract with the seller and it is normal to include an inspection contingency in your offer.

You will need to find a good agent to walk through the property, and send you videos (One that you can trust)Get a solid inspection, identify contractors that will give you bids for any big-ticket items prior to you hitting contingency dates. 

@Waylon Zook Based on inspection, I currently have single ply modified bitumen.

I actually got a $3500 seller credit after the inspection showed some repairs.

Oak park can be tricky, so you will want to ask the seller to get the compliance inspection done as soon as possible in the process.

Unless there was an inspection at move in you will have difficulty keeping any of the deposit.

Then (and only then) they will release the tax returns and maintenance reports and allow me to inspect them.

I would suggest getting a pest inspection, and home inspection that has photos included, then have the agent upload those and note "bids on some items are available".

Should I send him a letter now saying that he has the right to an initial move-out inspection so landlord and tenant can be present so landlord can point out what he needs to repair for he to get more of his security deposit back?

@Ceaneh Alexis I use TLE Worryfree Home Inspections for all my inspections.