If you truly don’t believe the property will appreciate and that rents will increase faster than expenses you should NEVER buy that property.

The entire lots level has to be increased.

Value adds were a combination of market value increases, rentability increases, strategic maintenance and improvements during lease cycles, and property management.

It's usually better to earn $200 less a month for one year than to sit vacant for two months, particularly in the winter.Consider a bigger drop for a 6-month lease to get through winter, then increase rent or find a new renter in the spring when competition is hotter.

If the current rents are below market, maybe it’s time for some modest increases, from what I’ve heard many landlords do this gradually.

Four properties provide diversification, greater potential for appreciation, higher aggregate depreciation deductions, and increased cash flow over time but involve more management complexity and higher leverage risk.

From your options, #1 is a big sink of cash and I can't tell how much that increases you rent. #2 is a no due to cash flow negative. #3 is the way to go.

By accepting pets, it not only has it increased my cash flow per stay, but it has opened up my place for more bookings. 

With inventory slightly decreasing in November, do you anticipate increased competition heading into the new year, or are higher mortgage rates keeping activity balanced?

Based on a gut check (checking the town population + location on google maps), this may be the case.