I am looking into making some repairs and then offering an allowance for new flooring and appliances, while listing a higher asking price to make up the difference.

Their analysis of the after repair value and desirability of the area will be invaluable if you don't live there.

I could of course keep repairing the slate when leaks appear every 2 years in different parts of the roof but it's a little stressful when we are on vacations and I think I'm time for a replacement.

None of the properties need major repairs.

I am really afraid about hiring a realtor who is not truthful about my home value after repair.

Higher/more frequent repairs etc.... thoughts....?

Then repair the damaged areas.

@David OlsonI am in no way an expert at this but I believe when you are making a cash purchase the main team players are:Attorneys, Title Company, Inspector and Appraiser (occasionally)Attorneys: Using legalese to get the purchase contract in writing Title Company: Perform due diligence to make sure there are no liens against the propertyInspector: You already covered thatAppraiser: To determine the price of the property at its current state and after repair value.

I was able to finance up to 80% of the after repair value. 

The best terms I have seen my clients get is a $50 / unit / month flat rate fee for management, and the worst was one property management company that quoted 10% per month of collected income, plus a 1 month rent "lease renewal fee", plus 10% of any repair costs.