Like others said I think the main thing is that you are inquisitive now, shows you will likely make it somewhere, good luck!

Main problem here is that I don't have money for the down payment.I would really love any advice people might have for me.

You need at least ten for resale purposes especially if tenant wants a lot of TI.No legal advice given.

But at some point down the road, we'd like to make real estate our main focus. 

I purposely staggered the leases to expire 2 months apart, and I made them shorter so that I could get a feel for the tenants and address any issues with a new lease if they opt to stay on.

I had spent the last year or so down there for my company doing the renovations to the old court house on East Main St. 

It is more economical to do it all at once.Winterizing often leaves you with some cracked fittings or faucets in the basement, which are easy to replace, but the main goal is to preserve the water heater, toilets and the in wall plumbing from frost damage.

If you're having the roofers come in after you do the tearoff, make sure the dumpster is there for them as well... they'll have cut pieces of new shingles and similar stuff to get rid of.I have also seen a couple of dumpster companies that offer a lower rate if all you're putting in it is shingles, no general trash - I suspect they are hauling it to either a recycling plant or a construction and demolition landfill, which is cheaper for them than a general-purpose landfill. 

Tax assessor values are for the purpose of collecting taxes. 

I prefer it for two main reasons:1.