I just bought a building with my sister where we are 50/50 partners but I am managing as it is in my location.

All are operated by management company.I hope that makes sense!

I have a decent understanding of it all and some sample documents but would greatly appreciate some guidance with closing this deal. 

Tenant Management: What have you learned about managing tenants effectively while sharing the same property?

Echoing more of the same - We manage 65+ units ranging from $80 a night to $2,000 a night we typically get negative reviews on a monthly if not weekly basis. 

The monthly HOA covers: Association Management, Insurance, Maintenance Grounds, Sewer, Security, Taxes, Trash, and water.What next steps would you guys take to get a better idea about this deal?

I would like to know if you would advise such an investment which has to be managed mostly remotely.

Sourcing deals and bandwidth (managing multiple projects) becomes your problem.

i hear hostaway works good. i just manage my own on 2 OTA platforms. pretty much all is streamlined on there. just have to keep up responsiveness and price optimization. but you could always hire out to a co-host if that would be worth your time. 

You can also call your property manager if you use a professional management company to see if their portfolio has anyone that recently purchased or currently owns properties in the area that are thinking about selling (just to help you rationalize your value better).