You go to their website, enter all the details of your deal(you have to have the deal under contract and it CANNOT be listed with an agent in the MLS), and someone will contact you in a day or two to ask you some questions.

I've seen at least two other big HOAs vote on this idea this year as well. 

Any advice regarding the pros and cons of these two cities?

This is obviously much better than $1,400 per month.On top of that, you will now get 2x the depreciation write-off so your taxes should go down.On top of that, you will now get 2x the appreciation when real estate price go up.On top of that, your tenants are helping you pay down the loan, initially at about $100/mo for both properties, which gradually gets better and better.On top of that, you now have more units so if one or two goes vacant, you have more renters covering the losses of the vacant units.If you want to keep these properties, I would do a cash-out refi and go buy more rental real estate.

If you are going to do the work, I would split the work in two - 1.

It’s easy to want to jump into big deals right away, but starting with one or two smaller properties lets you learn the basics of real estate investing without getting overwhelmed.

I currently own and self-manage two STRs in Maine and should be closing on a small 'cabin campground' with 10 cabins nearby that will also be operated as STRs. 

Nobody wants to pay higher taxes or medical costs but sometimes its worth picking the less costly of the two and calling it a win. 

My experience currently involves but is not limited to; breach of contract, embezzlement, coercion to include extortion and blackmail, and bribery from both lender and two NEW WESTERN agents.

I have gotten two very good clients that way.. this way I dont spend a dime on marketing they come to me :)