Here's a list of the improvements:-Replaced the roof-Landscaped the front yard with new sod, shrubs, flowers, mulch, etc.

There should be a plan to replace the roof 10 years from now and the parking lots 15 years. 

I have a handy man I generally use for repair work, but I'm a bit dubious about his insurance situation and am hesitant to have him on any roofs.

Years ago I had a roofing company and a number of hot tar kettles.

But I still think that would be tough road to hoe if you need to prove that they should be liable for failure to disclose an issue.After all, you wouldn't have to disclose a leak roof if you had paid someone to fix the roof.

We fixed a lot of other things in the house that are more important like the plumbing, the roof, the garage door, etc.  

Has a brand new roof, but the furnace is original (38 years old), and the water heater is 14 years old, so those things are going to be costly in the next few years. 

If you want to purchase rentals you are going to need that extra cash for an emergency fund in case you need to replace a roof or a water heater goes out, or for any vacancies because these things will happen.  

Having already been through this before I know they will hit is for missing siding, the whole said of the front building needs to be re-graded, the roof needed replacement and is causing water damage.

And you're going to need to start building a relationship with your local banks now anyway so you can add more houses.The sooner you do, the better.