My dilemma is to convert before winter OR save up and do it next fall.

My main concern is if somebody would fall off the railing(which is on my side) and sue me.

You'd think this house was falling apart.  

I have seen many investors fall flat because they tried to rehab from 3 time zones away!

@Jess F. - all mortgages will have a seasoning period; meaning you won't be able to immediately refinance.

Spring or fall is generally the best time around here.Depending on your demographic you could get different tenants. as you said, July/August could catch incoming students.

I do, however, advise waiting until you are able to find or create a great deal that you can afford before investing, and those type of deals don't just fall into your lap, you must work and actively seek them out ... the sooner and harder you start looking for them, saving for them, and educating yourself on how to spot and find them, then the sooner you will find them.

Be prepared to spend some money on inspections and that the first deal or two may fall through.

You should have a number of ways to acquire a property so you don't let anything fall through.

I understand seasonality has an impact as we head into the Fall however this year it seems a bit different.