If you look at my posts, I have a nice sized rental portfolio so I am very familiar with all the ins and outs as I share on here a lot of my experience in the area. 

Depreciation is a deduction against passive income (Sch E), and it is never "written off against ordinary gains" (which is not a correct expression either way).Here is the IRS Publication 527 link.Dealing with HOA is not my area of expertise, but I suggest to approach them nicely.

There are lots of nice resort-style condo communities that welcome renters in that range, though.

They only rent out 1 unit and keep the other one open for when they come to the area to visit family a couple of times a year, though they've never made the trip while we've lived here for the last 5 months.  

We spent around $30-40k just in the last year and a half alone as my wife and I were planning on making this our long term house (we didnt anticipate buying a business and moving out of town) and also making this a show piece with upgrades, nice carpentry etc to show people the work Im capable of in the RE world. 

Those who use the campground as a home base while they visit an area and those who choose a campground based off what the place offers.  

I'm now a licensed real estate agent with Exit Realty Metro (MN) and Homestead Realty (WI)) I am by no means rolling in cash (and proudly enjoy Sports Clips haircuts and obsessing about airline miles for my vacations) but real estate has helped me catch up on my retirement savings and provides a nice second source of income, which helps me stress less about taking on as many clients in my day job (or charging those clients a ton of money).My day job: I’m a political consultant that has managed campaigns, led field programs, designed trainings, or consulted on over 50 campaigns in 18 US states and 8 countries.

You might only be a couple blocks from the nice area, but it is still close enough where the hipsters want to live there because its cool. 

I know the house hacking concept but we rent in a really nice neighborhood and we have no plans for buying primary residence, I was want to start rentals buy and hold for passive income later refi and get the next one ans so on....

Sometimes it takes a few years to get even but a great place to visit!