Is there any reference I can consult for guidance on these issues?

We do not lend on STRs and we routinely refer folks to Mark at Visio. 

What you've shown here is not really a cause for concern in my eyes, however I see much worst conditions regularly.

@Ankush R.Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

Normal wear and tear refers to deterioration over time from ordinary use, but damage like a large oil stain in the driveway from a vehicle is preventable and would fall under tenant responsibility.

I was referred to Hostaway by some people who have had a great experience with it.

I'd focus on getting a better property manager, their job is to shield you from most of these headaches and to prevent them in the first place through tenant selection and doing regular property inspections.

Property Management Company we work with right now to manage is fine with regular rental but I am having hard time working with them on student rental where some of the regular renting rules don't generally apply. 

What are you referring to when you say more affordable housing?  

Begin small by making regular contributions to build your portfolio over time.