When it comes to the initial phone call when dealing with off market deals from direct owners, is it always better to pick up the physical phone and dial out to reach them, or would a robo dialer with a pre -recorded message be more efficient?

On the flip side of that axis, high appreciation properties often generate cash relatively "poorly" as they are in limited supply areas (like a peninsula or an island or a ski resort) and more and more buyer types want to own them and are willing to "overpay" and ignore rental production potential.

Not to say I'll stop investing there, but this initial part of my portfolio is going to be built to protect me in the long term.Great point about the FHA, I haven't actually gone through a pre-qual for that so if you have a great FHA lender, I'd love to give them a look!

Do you use a pre-built tool or did you create something yourself? 

First step is to get a pre-approval to determine your max spend then you can determine where you are a comfortable monthly.

Summer is prime rental season and we will use it for cross-country skiing in the winter time.

I was hoping to find a calculator that had something where you could put how much money you currently have, how much you plan to add monthly or yearly, and then show what happens if you pay cash versus finance them and shows monthly or yearly cash flow for both options, but I might just have to do this on a spreadsheet if a pre-built one doesn't exist. 

The lender provided a "pre-application worksheet" with a breakdown of our likely closing costs and they are MUCH higher than we expected.

I came across a 2.99% APR, 5% down option, with NO PMI through a local bank, however, it is an adjustable rate mortgage that is subject to change every 5 years.

The following is a very cursory list of how I would approach this.1) Work with a real estate agent to do thorough research on sales prices (comps) for similar properties in the area.2) Work with an experienced RE consultant or developer to create a pro-forma based on solid research for your development that includes 1) a pre-development and development budget that includes a) soft costs like architect and engineer fees, geotech, permits, survey, builders risk insurance, legal, etc. and b) hard costs (construction costs); 2) sources and uses of funds; 3) cash flows; 4) sales (absorption) projections; and 5) a capital accumulation model for your different development scenarios to help determine which alternative would yield the highest investment return.3) Find a reputable architect and engineer to create drawings and help you through the permitting process.4) Submit drawings to GCs for bid.5) Update your pro-forma for the estimated construction costs and take it to several lenders to determine what the loan terms would be.6) Secure a loan, hire a GC, and start building.Again, the above is just a simple general overview and is not meant to be comprehensive by any means.