I'm sure at some point handling these calls will become second nature but in the mean time I'll do my best and just learn from my mistakes. 

On the handyman... through trial and error you will find one naturally but there are online websites where contractors can bid on jobs and are reviewed for their work.

Plus its a beautiful town, prices seem entirely reasonable, plenty of tourism in summer for hiking, nature, events, etc and the same in winter for skiing, snowmobiling, and the likes.  

A quick walk through and I estimated about $60K in rehab, where as I want to spend about $10K-$15K improving the back yard to the lake (20ft. bulkhead, 12ft x 30ft deck, covered patio with natural gas grill).Here are MY numbers ( I need to buy the property for about $60k-$70K)Buy for $60K, rehab for $60K in $120k sell for $180K-$199K!

We do this by working with people to find solutions, creatively if necessary, to accomplish win-win outcomes for them and us by buying properties that are either naturally great deals or that need some rehabbing.

Soon networking will become second nature.

I also have found local lenders aremore expensive than national lenders because of conservative nature so best route is really private money.

@Hersh M. for me, rather than trying to predict the market based on previous cycles, I would highly recommend investing (particularly in today's market) for cash flow, or forced appreciation - NOT natural appreciation.There are a lot of people that believe that we are in the 9th inning - specifically for large multi-family markets - and if that's the case and the market shows a correction, it will be key for people to be able to carry the expenses of their rentals no matter what the market's valuation is of the property.However, for people that are investing hoping that their properties are going to go up, since that's what happened over the past 7+/- years, that is typically where we see bubbles forming.I am not sure that answered your question of where we are in the market, but I do believe that's one of the reasons that causes a lot of market cycles to form.

Now back to the real, or at least more consistent world: drywall costs vary as to the unique nature of each job location, therefore comparing estimates without details is an exercise in futility. 

What are the cost & nature of the upgrades?