You'll want to understand what kind or notices and documents you need to get executed to either up their rent or turn the unit.Solid long term tenants are worth their weight in gold in my book so if theres a way to up the rent and keep them happy I's say thats the best route personally.

They apply, but you are just subject to gift tax at that point, which does not actually result in a tax bill for you, but a reduction in your total giftable allowance which is ~13M dollars. 

Does this guidance carry any weight? 

While vacation rentals aren't a huge drop in the home supply bucket, they're not nothing, and any reduction in home supply for primary residences will eventually push prices up.

Future Cashflow (rate reduction)

My realtor is worth his weight in gold and works very hard when I have a deal going with him.

You might add the weighted interest you are currently paying, to see if you actually save money by refinancing your primary.For your 1st investment property, if you want to do a cash out Refinance on a DSCR type loan, you will need to get a minimum loan of $70,000, at 6.6%, you would need to have the property rented for a minimum of $900/mo, assuming taxes are about $2k/year, and Insurance is $750/yr. 

For some lenders, a 3 year prepay is neutral on the rate as as factor and a 5 year prepay is a 1/2 point reduction, a 4 year prepay is a .25 reduction and a 2 year prepay is a .25 add to the rate and a 1 year prepay is a .5 add to the rate.

The installer did not remove the original weights from the original 100 year old windows nor did he insulate the weight shafts which is a must in Northern New Hampshire where temperatures often drop to -20.

However, HUD will allow for a reduction in the offer if a problem that's unknown now crops up after the offer has been accepted - I know several people (including my mother) that got some money off their HUD deal.