How much you intend to scale is an important consideration.

Also, your property taxes will likely rise, unless you are purchasing the property for less than it's current assessed value (I've only managed to do this once).  

Hard costs can go up considerably if you have to blast rock for foundations and haul massive amounts of dirt.

Another consideration would be to find a wholesaler who would be willing to mentor you.Just a few thoughts

Another consideration is if it really makes sense for him from an investment stand point.

I also used my VA loan, so I only had to pay closing costs of about $3.5k.Unfortunately, this area was in what’s called a “Mela-roos tax” zone for roads/neighborhood upkeep which added an extra $350/month to my PITI.Therefore, my total payments were $1600/month.When I moved in the summer of 2012, it looked like mortgage rates had sunken to about as low as they would go (I was wrong, they dropped another .75 basis points…but who can time the market).I decided that I would refinance to get a lower monthly payment.For $2k, I was able to reduce my monthly payments by $230.Add this to the fact that real estate prices were rising fast (my Ohio property was now worth about $95k and the one in California was at about $240K!).

In my state, property taxes can be low due to Homestead tax exemptions on primary residence, especially if the owner has lived there a considerable time, because there's a cap on tax increases each year for homesteads.It's always a good idea for agents to forewarn buyers not to rely on property tax estimates long before closing.

I would start looking at areas where you could maintain that day job and then compare the price/rent ratios in those areas as well as take into consideration the potential for appreciation.

Definitely taking it into consideration. 

Lots of these funds get very, very complicated - and the costs rise to match.