Speaking just about the cost, yes, $3500 is probably in the rough ballpark to have a number of rooms professionally paint. 

We noted lately that the staircases are slippery, probably the carpets are worn out and have lost the traction, may be?

I think house hacking is a great way to get started investing and you could probably get started sooner than you think with some of the low down payment programs available today. 

They probably wont allow you to use an assignable contract so you'd have to double close or buy outright and then resell.

You could also simply give notice that at the end of their lease the rent will be increased by $1,000, which would probably have them move out anyway at the end of their lease.

Student housing is probably still a sound investment, just don’t expect the dramatic increases seen last year in students from India to happen every year. 

@Kyle Pockat The reality is that if buyers are willing to "overpay", they're probably not overpaying at all. 

My property will probably only appraise for $50K.     

Never risk your integrity to make a sale, one deal will never make you rich, but losing your reputation and integrity will probably leave you broke. 3.)

With the 4-plex: Once acquired, take the time to stabilize, maximize rents, minimize expenses and learn what is most probably the hardest thing about real estate industry: managing tenants and all their quirky little idiosyncracies!