I’ll be sure to ask other investors about how the process works with the historic board, luckily I know another investor in town who has dealt with them.Our plan may eventually be to cut up this building into multiple residential dwellings if the city allows.

I don't have experience with it, but I would imagine those policies would be a lot higher higher than a traditional dwelling policy. 

So, if I were to sell it by 2020 (within 3 years of turning it into rental), I pocket the entire capital gains on the property (roughly $65k) but I will instantly lose my $750/monthly cash flow from rent as well as all other tax deductions and depreciation I could benefit from each year. 

It may be a bit more difficult to find a lender that will issue a HELOC on a non-owner occupied dwelling, but I'm sure you can find one.

I had a dream, which was not all a dream.The bright sun was extinguished, and the starsDid wander darkling in the eternal space,Rayless, and pathless, and the icy earthSwung blind and blackening in the moonless air;Morn came and went—and came, and brought no day,And men forgot their passions in the dreadOf this their desolation; and all heartsWere chilled into a selfish prayer for light:And they did live by watchfires—and the thrones,The palaces of crowned kings—the huts,The habitations of all things which dwell,Were burnt for beacons; cities were consumed,And men were gathered round their blazing homesTo look once more into each other's face...

The main difference between the homeowners policy (HO3) and dwelling policy (DP) is the occupancy.

Commercial loan for 80% of value.Rent $1050/monthThe policy choices: Cost Policy A $726 annually Policy B $1,008 annually Coverage: dwelling $113,296 $352,300 Other Structures $2,000 $35,230 Personal Property $1,500 $3,000 Loss of Rents $22,659 $35,230 Landlord Liability $100,000 $500,000 Medical Payments $500 $5,000 Deductible $500 $1,000

You what you want with your instant collection.

Much less commonly used.Most Personal policies (Homeowners & Dwelling Fire) from the companies providing the best rate (on a per $1000 of coverage basis) will be written on Replacement Cost.

I bought a Whirlpool last fall and had instant burner ignition problems.