Any advice as to what others do on a seasonal or yearly basis would be super helpful.

He called and emailed me every day.

. #1 would call in sick every day to fool around with the wife.

You don't owe taxes when you inherit the property, but there are other tax issues you need to manage such as step-up of the basis. 

Have your AC contractor show up for the inspection to advise on what might be problematic for them in installing the duct work and get a quote.I deal with these older properties - both residential and commercial - everyday so it's less of a threat than a "don't lick the walls and don't snort the siding."   

No one has more "skin in the game" than a PMC as they have to deal with the property every day until an owner sells or fires them.Also recommend finding your own Inspector and not one referred by an agent.

There is a property for sale that I drive by everyday and I am not sure if it’s worth diving into/if it could be a good deal.  

I see them everyday.

There is a reason on a sq ft basis that bachelors usually fetch a higher rent per sq ft. over a 2 bedroom.

If your property is in tough shape or is older; I would increase this reserve, but this is a rough calculation for a property that is in good condition, not in need of major capex.You can also increase this annually or do it on a monthly basis; i.e. $25 per unit, per month goes into a savings account and I will increase that x% per year.