Percentage of the purchase price), average home in Cleveland purchased in 2014 or the average home purchased in San Diego in 2014.  

I recently received a quote to paint the entire interior of my recently purchased home.

I see this is an older post (better late than never) Usually 1% of the purchase price is reasonable.

2) Do you hire a property management company before or after you purchase the property? 

I actually have done personally exactly what you're describing - HELOC on primary residence, use that to purchase new primary, move into new primary and rent the previous home(4 times in 5 years).

I am consistently helping my investor clients purchase move in ready 3/2/2 SFR's here for less than $300K.

I just purchased a unit in the Mount Vernon area close to Ft.

If you can swing it and are willing to do what it takes to not lose the property if sh** hits the fan, then I would highly suggest purchasing in a more desirable area. 

I have 10 acres of raw land that I purchased to put a house on that already has a well, power and septic available. 

There's always the more expensive reverse 1031 exchange but need to be able to purchase on the front end before selling.