@Theresa SanfordI have had great success of what you already mentioned which is painting the exterior.  

But, you could spend money maybe on the exterior, roof, car park to make it more attractive for a tenant.

@Rose Martin - when you say "shutters" are you referring to exterior shutters or interior window treatment?  

I'm not talking about 'over-building' for the comps in the area; I'm talking about having a generous attitude towards your buyers, as opposed to having a penny-pinching attitude.  

HOA makes sure the exterior of the house stays looking good and usually keeps a lid on anti-social activity, if any.  

For the most part though,  they only have to approve exterior changes such as paint color, fences, roofing material.  

New fixtures throughout interior and exterior.

Also, change the exterior door locks as soon as you can after closing.  

Students would be your safest option in Barrie as opposed to welfare which is the most common other option for rooming houses.

All details would ofcourse be in a contract.Pro's - I secure a tenant now as opposed to later- I work on rehab less Cons - I would have to trust his work, or micromanage repairs- He is a very busy individual, with loud work trucks and a lot of equipment to disturb surrounding tenantsAs tempting as this sounds, is it even legal to rent an unfinished space?