Is there an inspection of some sort or do I need to ask the condo association for maintenance records?

I'd refer them to petscreening.com and let them sort out the ESA letter.

Selecting bad PM's and now considering selecting a bad tenant...

Guarantee a note personally sort of defeats the purpose of utilizing a remote entity, at least for the liability created by the note.  

The type of cleaning service would depend on the property that is selected.

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

You can invest in any market selecting the ones that you believe are seeing the most growth, and do it from anywhere.

It is the only calculator of its kind to help you determine: if househacking is a better investment than a traditional home purchase, how long to hold onto the investment before selling, how long to live in the property, and which unit to occupy.If this will be a traditional rental property investment (not a househack), select ‘renter’ for all units under the Summary Tab’s ‘Property Information’ section.Metrics used for the deal analysis:The purchase price is based on the median sale price - $1,450,000 Unit bed/bath counts are based on the median 5 bed/3 bath counts for sold Astoria 2-family properties this year.Projected rents are $3,200 and $3,900 respectively as shown in our median rents for 2 bedroom and 3 bedroom apartments.Not included in the analysis is ADU income.

Should I try to have him fill out a W9 and sign some sort of contract since money over $600 is being exchanged for services? 

You will probably have some sort of limit regarding mold/medical, but thee things can turn into a mess, trust me, I manage a lot of units and have done so for almost 30 years.